几种新杂环化合物的金属催化合成研究
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摘要
Sonogashira偶联反应自发现以来,经过广泛、深入的探索与研究,已日臻完善。Sonogashira反应具有条件温和、操作简单、高效等特点,在杂环化合物、天然产物的合成、光电材料以及纳米分子器件等领域的应用极为广泛,已成为有机合成中最为有效的反应途径之一。然而,在该领域中仍有一些有待进一步研究和解决的课题,主要集中在两个方面:一是研究高效、经济、环保的非Pd催化体系;二是寻找和筛选能够在温和条件下有效催化不活泼卤代芳烃,特别是氯代芳烃的催化体系。本论文主要从这两方面入手,对铁催化的C–C键形成进行了研究,主要分为以下三部分:
1、分别综述了Sonogashira偶联反应中催化剂的发展和氯代芳烃偶联反应的研究进展。
2、基于酞嗪杂环衍生物具有重要的杀虫、杀菌、抗病毒和植物生长调节等生物活性,我们研究了Pd、Fe催化的1,4-二氯酞嗪与不同末端炔的Sonogashira偶联反应。研究以寻找新催化体系为目标,主要探索了催化剂、溶剂、碱、温度等对催化体系的影响,发现Fe可以代替Pd使用,反应结果较为理想。研究中合成了4种新型酞嗪杂环衍生物,并通过元素分析、IR、1H NMR、13C NMR、MS和X-射线衍射分析系统表征了其化学结构。
3、鉴于嘧啶杂环衍生物具有广谱的生物活性以及在超分子构筑中所呈现的独特结构,我们研究了Pd、Fe催化的2-氨基-4,6-二氯嘧啶与不同末端炔进行的Sonogashira偶联反应,发现FeCl3/C的催化效果不很理想,而Pd/C作为催化剂可以高效催化该氯代芳烃的Sonogashira偶联反应,对催化体系亦是一种有意义的改善。研究中合成了4种新型嘧啶杂环衍生物,并通过元素分析、IR、1H NMR、13C NMR、MS和X-射线衍射分析系统表征了其化学结构。
本论文尝试采用Fe催化剂代替Pd催化氯代芳烃的Sonogashira偶联反应,对探索新金属源在偶联反应中的应用具有重要意义。
Since the discovery of Sonogashira coupling reaction, it has been widely investigated and applied in the synthesis of diverse heterocyclic compounds, natural products, photoelectric materials as well as nano molecular devices. Sonogashira reaction was characterized by the mild conditions, simple operation and efficiency. However, there are some challenges remained to be resolved, one of which is the exploration of novel inexpensive, environment friendly and efficient catalyst systems. Additionally, to find new efficient catalysts for coupling of unreactive chlorinated arenes with terminal alkynes is also the focus within this field. In view of the two aspects, we carried out the studies on the metal-mediated carbon-carbon bond formation.
In the first section, recent research of Sonogashira coupling reactions was reviewed briefly in both the improvement on catalysts and the coupling reaction of unreactive chlorinated arenes.
In the second part, we studied the Sonogashira coupling reaction of 1,4-dichloro- phthalazine with various terminal alkynes, recognizing the important bioactivity of phthalazine derivatives in the antimicrobial, antiviral reactivity and plant growth adjustment. Through the optimization of reaction conditions such as catalyst, ligand, sovent, base and temperature, the coupling reaction catalyzed by the FeCl3/C can give moderate yields. Four new phthalazine derivatives were synthesized and fully characterized by IR, 1H NMR, 13C NMR, MS, elemental analysis and X-ray diffraction techniques.
In view of the unique structure and bioactivity of pyrimidine derivatives, the third section is the evaluation of 2-amino-4,6-dichloropyrimidine coupling with different terminal alkynes. It was found that iron catalyst does not work well with this system giving unsatisfactory yields, but the Pd/C catalyst is a good choice for improving this coupling reaction. Four new pyrimidine derivatives were obtained and fully identified by IR, 1H NMR, 13C NMR, MS, elemental analysis and X-ray diffraction techniques.
In summary, the studies about the Sonogashira coupling reaction catalyzed by iron are of significance for the exploring and of new metal source in coupling reactions.
1、分别综述了Sonogashira偶联反应中催化剂的发展和氯代芳烃偶联反应的研究进展。
2、基于酞嗪杂环衍生物具有重要的杀虫、杀菌、抗病毒和植物生长调节等生物活性,我们研究了Pd、Fe催化的1,4-二氯酞嗪与不同末端炔的Sonogashira偶联反应。研究以寻找新催化体系为目标,主要探索了催化剂、溶剂、碱、温度等对催化体系的影响,发现Fe可以代替Pd使用,反应结果较为理想。研究中合成了4种新型酞嗪杂环衍生物,并通过元素分析、IR、1H NMR、13C NMR、MS和X-射线衍射分析系统表征了其化学结构。
3、鉴于嘧啶杂环衍生物具有广谱的生物活性以及在超分子构筑中所呈现的独特结构,我们研究了Pd、Fe催化的2-氨基-4,6-二氯嘧啶与不同末端炔进行的Sonogashira偶联反应,发现FeCl3/C的催化效果不很理想,而Pd/C作为催化剂可以高效催化该氯代芳烃的Sonogashira偶联反应,对催化体系亦是一种有意义的改善。研究中合成了4种新型嘧啶杂环衍生物,并通过元素分析、IR、1H NMR、13C NMR、MS和X-射线衍射分析系统表征了其化学结构。
本论文尝试采用Fe催化剂代替Pd催化氯代芳烃的Sonogashira偶联反应,对探索新金属源在偶联反应中的应用具有重要意义。
Since the discovery of Sonogashira coupling reaction, it has been widely investigated and applied in the synthesis of diverse heterocyclic compounds, natural products, photoelectric materials as well as nano molecular devices. Sonogashira reaction was characterized by the mild conditions, simple operation and efficiency. However, there are some challenges remained to be resolved, one of which is the exploration of novel inexpensive, environment friendly and efficient catalyst systems. Additionally, to find new efficient catalysts for coupling of unreactive chlorinated arenes with terminal alkynes is also the focus within this field. In view of the two aspects, we carried out the studies on the metal-mediated carbon-carbon bond formation.
In the first section, recent research of Sonogashira coupling reactions was reviewed briefly in both the improvement on catalysts and the coupling reaction of unreactive chlorinated arenes.
In the second part, we studied the Sonogashira coupling reaction of 1,4-dichloro- phthalazine with various terminal alkynes, recognizing the important bioactivity of phthalazine derivatives in the antimicrobial, antiviral reactivity and plant growth adjustment. Through the optimization of reaction conditions such as catalyst, ligand, sovent, base and temperature, the coupling reaction catalyzed by the FeCl3/C can give moderate yields. Four new phthalazine derivatives were synthesized and fully characterized by IR, 1H NMR, 13C NMR, MS, elemental analysis and X-ray diffraction techniques.
In view of the unique structure and bioactivity of pyrimidine derivatives, the third section is the evaluation of 2-amino-4,6-dichloropyrimidine coupling with different terminal alkynes. It was found that iron catalyst does not work well with this system giving unsatisfactory yields, but the Pd/C catalyst is a good choice for improving this coupling reaction. Four new pyrimidine derivatives were obtained and fully identified by IR, 1H NMR, 13C NMR, MS, elemental analysis and X-ray diffraction techniques.
In summary, the studies about the Sonogashira coupling reaction catalyzed by iron are of significance for the exploring and of new metal source in coupling reactions.
引文
[1] (a) Zapf, A.; Beller, M. Top. Catal. 2002, 19, 101?109. (b) Br?se, S.; Kirchhoff, J. H.; K?bberling, J. Tetrahedron 2003, 59, 885?939.
[2] Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313?3315.
[3] Cassar, L. J. Organomet. Chem. 1975, 93, 253?257.
[4] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467?4470.
[5] (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49. (b) Tykwinski, R. R. Angew. Chem. Int. Ed. 2003, 42, 1566?1568.
[6] Plenio, H. Angew. Chem. Int. Ed. 2008, 47, 6954?6956.
[7] Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133?173.
[8] (a) Doucet, H.; Hierso, J.-C. Angew. Chem. Int. Ed. 2007, 46, 834?871. (b) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874?922. (c) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283–2321.
[9] Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551?8553.
[10] Xia, M.; Wang, Y. G. Chin. J. Org. Chem. 2003, 23, 609?612.
[11] Elangovan, A.; Wang, Y.-H.; Ho, T.-I. Org. Lett. 2003, 5, 1841?1844.
[12] Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219?224.
[13] Anastasia, L.; Negishi, E. Org. Lett. 2001, 3, 3111?3113.
[14] (a) Dai, W.-M.; Guo, D.-S.; Sun, L.-P. Tetrahedron Lett. 2001, 42, 5275–5278.
[15] Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39?46.
[16] (a) Nájera, C.; Gil-Moltó, J.; Karlstr?m, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451?1454. (b) Gil-Moltó, J.; Nájera, C. Eur. J. Org. Chem. 2005, 4073?4081.
[17] (a) Wang, R.; Piekarski, M. M.; Shreeve, J. M. Org. Biomol. Chem. 2006, 4, 1878?1886. (b) Rau, S.; Lamm, K.; G?rls, H.; Sch?ffel, J.; Walther, D. J. Organomet. Chem. 2004, 689, 3582?3592.
[18] Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411?1414.
[19] Li, J. H.; Hu, X.-C.; Liang, Y.; Xie, Y.-X. Tetrahedron 2006, 62, 31?38.
[20] Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391?393.
[21] Dibowski, H.; Schmidtchen, F. P. Tetrahedron Lett. 1998, 39, 525?528.
[22] Bleicher, L.; Cosford, N. D. P. Synlett. 1995, 1115?1116.
[23] López-Deber, M. P.; Castedo, L.; Granja, J. R. Org. Lett. 2001, 3, 2823?2826.
[24] Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron. 2001, 57, 8017?8028.
[25] Soler, R.; Cacchi, S.; Fabrizi, G.; Forte, G.; Martín, L.; Martínez, S.; Molins, E.; Moreno-Ma?as, M.; Petrucci, F.; Roig, A.; Sebastián, R. M.; Vallribera, A.Synthesis 2007, 3068?3072.
[26] Kim, J.-H.; Lee, D.-H.; Jun, B.-H.; Lee, Y.-S. Tetrahedron Lett. 2007, 48, 7079?7084.
[27] Cai, M.; Xu, Q.; Sha, J. J. Mole. Catal. A.: Chem. 2007, 272, 293?297.
[28] Cassar, L. J. Organomet. Chem. 1975, 93, 253?257.
[29] (a) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. Tetrahedron Lett. 1992, 33, 5363?5364. (b) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716?4721.
[30] Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315?4317.
[31] Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727?4729.
[32] Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843?3846.
[33] Ma, D.; Liu, F. Chem. Commun. 2004, 1934?1935.
[34] Biffis, A.; Scattolin, E.; Ravasio, N.; Zaccheria, F. Tetrahedron Lett. 2007, 48, 8761?8764.
[35] (a) Li, J.-H.; Li, J.-H.; Wang, D.-P.; Pi, S.-F.; Xie, Y.-X.; Zhang, M.-B.; Hu, X.-C. J. Org. Chem., 2007, 72, 2053?2057. (b) Tang, B.-X.; Wang, F.; Li, J.-H.; Xie, Y.-X.; Zhang, M.-B. J. Org. Chem., 2007, 72, 6294?6297.
[36] Thakur, K. G.; Jaseer, E. A.; Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2009, 50, 2865?2869.
[37] Chen, H.-J.; Lin, Z.-Y.; Li, M.-Y.; Lian, R.-J.; Xue, Q.-W.; Chung, J.-L.; Chen, S.-C.; Chen, Y.-J. Tetrahedron 2010, 66, 7755?7761.
[38] Zuidema, E.; Bolm, C. Chem. Eur. J. 2010, 16, 4181?4185.
[39] Beletskaya, I. P.; Latyshev, G. V.; Tsvetkov, A. V.; Lukashev, N. V. Tetrahedron Lett. 2003, 44, 5011?5013.
[40] Wang, L.; Li, P.; Zhang, Y. Chem. Commun. 2004, 514?515.
[41] de Souza, R. O. M. A.; Bittar, M. S.; Mendes, L. V. P.; da Silva, C. M. F.; da Silva, V. T.; Antunes, O. A. C. Synlett. 2008, 1777?1780.
[42] González-Arellano, C.; Abad, A.; Corma, A.; García, H.; Iglesias, M.; Sánchez, F.Angew. Chem. Int. Ed. 2007, 46, 1536?1538.
[43] Li, P.; Wang, L.; Wang, M.; You, F. Eur. J. Org. Chem. 2008, 5946?5951.
[44] Park, S.; Kim. M.; Koo, D. H.; Chang, S. Adv. Synth. Catal. 2004, 346, 1638?1640.
[45] For general reviews, see: (a) Correa, A.; Manche?o, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108?1117. (b) Enthaler, S.; Junge, K.; Beller, M. Angew. Chem. Int. Ed. 2008, 47, 3317?3321. (c) Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500?1511. (d) Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624?629. (e) Bolm, C., Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217?6254.
[46] (a) Cahiez, G.; Foulgoc, L.; Moyeux, A. Angew. Chem. Int. Ed. 2009, 48, 2969?2972. (b) Volla, C. M. R.; Vogel, P. Angew. Chem. Int. Ed. 2008, 47, 1305?1307. (c) Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844?9845. (d) Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J. Org. Lett. 2005, 7, 1219?1222. (e) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856?13863.
[47] (a) Correa, A.; Carril, M.; Bolm, C. Angew. Chem. Int. Ed. 2008, 47, 2880?2883. (b) Correa, A.; Carril, M.; Bolm, C. Chem. Eur. J. 2008, 14, 10919?10922. (c) Mayer, A. C.; Salit, A.-F.; Bolm, C. Chem. Commun. 2008, 5975?5977. (d) Correa, A.; Bolm, C. Adv. Synth. Catal. 2008, 350, 391?394.
[48] Carril, M.; Correa, A.; Bolm, C. Angew. Chem. Int. Ed. 2008, 47, 4862?4865.
[49] Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2008, 73, 9061?9064.
[50] Volla, C. M. R.; Vogel, P. Tetrahedron Lett. 2008, 49, 5961?5964.
[51] Sawant, D. N.; Tambade, P. J.; Wagh, Y. S.; Bhanage, B. M. Tetrahedron Lett. 2010, 51, 2758?2761.
[52] Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176?4211.
[53] Sakamoto, T.; Shiraiwa, M.; Kondo, Y.; Yamanaka, H. Synthesis 1983, 312?314.
[54] Ames, D. E.; Brohi, M. I. J. Chem. Soc. Perkins. Trans. 1 1980, 1384?1389.
[55] Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818?819.
[56] Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127?14136.
[57] K?llhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem. Int. Ed. 2003, 42, 1056?1058.
[58] Remmele, H.; K?llhofer, A.; Plenio, H. Organometallics 2003, 22, 4098?4103.
[59] Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 42, 5993?5996.
[60] Anderson, K. W.; Buchwald, S. L. Angew. Chem. 2005, 117, 6329?6333.
[61] Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2004, 45, 8443–8446.
[62] Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P. Org. Lett. 2004, 6, 3473?3476.
[63] Yi, C.; Hua, R. J. Org. Chem. 2006, 71, 2535?2537.
[64] Komáromi, A.; Novák, Z. Chem. Commun. 2008, 4968?4970.
[65] Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem. 2008, 73, 6037?6040.
[66] Torborg, C.; Huang, J.; Schulz, T.; Sch?ffner, B.; Zapf, A.; Spannenberg, A.; B?rner, A.; Beller, M. Chem. Eur. J. 2009, 15, 1329?1336.
[67] Jin, M.-J.; Lee, D.-H. Angew. Chem. Int. Ed. 2010, 49, 1119?1122.
[1] (a) Daiber, A.; Oelze, M.; Coldewey, M.; Kaiser, K.; Huth, C.; Schildknecht, S.; Bachschmid, M.; Nazirisadeh, Y.; Ullrich, V.; Mülsch, A.; Münzel, T.; Tsilimingas, N. Biochem. Biophys. Res. Commun. 2005, 338, 1865–1874. (b) Bang, L.; Nielsen-Kudsk, J. E.; Gruhn, N.; Trautner, S.; Theilgaard, S. A.; Olesen, S.-P.; Boesgaard, S.; Aldershvile, J. Eur. J. Pharmacol. 1998, 361, 43–49.
[2] (a) Steyn, D. W.; Odendaal, H. J. Eur. J. Obstet. Gynecol. Reprod. Biol. 1997, 75, 155–159. (b) Wacker, J. R.; Wagner, B. K.; Briese, V.; Schauf, B.; Heilmann, L.; Bartz, C.; Hopp, H. Eur. J. Obstet. Gynecol. Reprod. Biol. 2006, 127, 160–165.
[3] (a) Gasiorowski, K.; Szyba, K.; Wozniak, D.; Gulanowski, B. Mutagenesis 1997, 12, 411–415. (b) Gasiorowski, K.; Brokos, B. Mutagenesis 2000, 15, 137–141.
[4] Saito, H.; Minami, M. Antihypertensive drugs today Ed. Saito, H. Koninklijke W?hrmann BV, The Netherlands, 1991.
[5] Piatnitski, E. L.; Duncton, M. A. J.; Kiselyov, A. S.; Katoch-Rouse, R.; Sherman, D.; Milligan, D. L.; Balagtas, C.; Wong, W. C.; Kawakami, J.; Doody, J. F. Bioorg. Med. Chem. Lett. 2005, 15, 4696–4698.
[6] Madhavan, G. R.; Chakrabarti, R.; Kumar, S. K. B.; Misra, P.; Mamidi, R. N. V. S.; Balraju, V.; Kasiram, K.; Babu, R. K.; Suresh, J.; Lohray, B. B.; Lohrayb, V. B.; Iqbal, J.; Rajagopalan, R. Eur. J. Med. Chem. 2001, 36, 627–637.
[7] Rodríguez-Ciria, M.; Sanz, A. M.; Yunta, M. J. R.; Gomez-Contreras, F.; Navarro, P.; Fernandez, I.; Pardo M.; Cano, C. Bioorg. Med. Chem. 2003, 11, 2143–2148.
[8]林国强,刘汉泉,杨细文,CN. 1523024A,2004–08–25.
[9] Chen, L.; Thompson, L. K.; Tandon, S. S.; Bridson, J. N. Inorg. Chem. 1993, 32, 4063–4068.
[10] Deng, Z.; Tseng, H.-W.; Zong, R.; Wang, D.; Thummel, R. Inorg. Chem. 2008, 47, 1835–1848.
[11] Barrios, A. M.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 11751–11757.
[12] (a) Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133–173. (b) Seki, M. Synthesis 2006, 2975–2992.
[13] (a) Sullivan, D. A.; Palenik, G. J. Inorg. Chem. 1997, 16, 1127–1133. (b) Okabe, N.; Fukuda, H.; Nakamura, T. Acta Cryst. 1993, C49, 1844–1845. (c) Kuzelka, J.; Mukhopadhyay, S.; Spingler, B.; Lippard, S. J. Inorg. Chem. 2004, 43, 1751?1761. (d) Barrios, A. M.; Lippard, S. J. Inorg. Chem. 2001, 40, 1060–1064. (e) Kuzelka, J.; Spingler, B.; Lippard, S. J. Inorg. Chim. Acta 2002, 337, 212–222.
[14] (a) Singelenberg, F. A. J.; van Eijck, B. P. Acta Cryst. 1987, C43, 693–695. (b) Pollagi, T. P.; Geib, S. J.; Hopkins, M. D. Acta Cryst. 1994, C50, 910–913. (c) Aaker?y, C. B.; Schultheiss, N.; Desper, J. Inorg. Chem. 2005, 44, 4983–4991. (d) Aaker?y, C. B.; Schultheiss, N.; Desper, J.; Moore, C. Cryst. Growth Des. 2007, 7, 2324–2331. (e) Aaker?y, C. B.; Schultheiss, N.; Rajbanshi, A.; Desper, J.; Moore, C. Cryst. Growth Des. 2009, 9, 432–441.
[15] Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. 1995, 34, 1555–1573.
[16] Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104–112.
[17] Sivakumar, R.; Gnanasam, S. K.; Ramachandran, S.; Leonard, J. T. Eur. J. Med. Chem. 2002, 37, 793–801.
[18]李学华,涂光忠,安东各,合成化学,2005, 13, 204–205.
[1] Gangjee, A.; Shi, J.; Queener, S. F. J. Med. Chem. 1997, 40, 1930–1936.
[2] Herbrecht, R.; Denning, D. W.; Patterson, T. F.; Bennett, J. E.; Greene, R. E.; Oestmann, J.-W.; Kern, W. V.; Marr, K. A. N. Engl. J. Med. 2002, 347, 408–415.
[3] (a) Gangjee, A.; Lin, X.; Kisliuk, R. L.; McGuire, J. J. J. Med. Chem. 2005, 48,7215–7222. (b) Gangjee, A.; Li, W.; Yang, J.; Kisliuk, R. L. J. Med. Chem. 2008, 51, 68–76.
[4]祁雪丹,屠树滋,王秋娟,中国新药杂志,2003, 12, 810–816.
[5]希尔艾力?买买提依明,硕士论文,新疆大学,乌鲁木齐,2008.
[6] (a) Levitt, G.; Baker, D. Synthesis and chemistry of agrochemicals II 1991, 16–31. (b)范志金,刘丰茂,钱传范,农药,1999, 38, 6–9.
[7] (a) Deng, F.; Hatzios, K. K. Pestic. Biochem. Phys. 2003, 74, 102–115. (b) Milliman, L. D.; Riechers, D. E.; Wax, L. M.; Simmons, F. W. Weed Sci. 2003, 51, 139–144. (c) Lun, A. F.; Chikoye, D.; Adesiyan, S. O. Weed Technol. 2005, 19, 122–127.
[8] Tamaru, M.; Saito, Y. Pestic. Sci. 1996, 47, 125–130.
[9] (a) Tamaru, M.; Takehi, T.; Masuyama, N. Pestic. Sci. 1996, 47, 327–335. (b) Nezu, Y.; Miyazaki, M.; Sugiyama, K.; Kajiwara, I. Pestic. Sci. 1996, 47, 103–113.
[10]魏青,李丽,高胜利,光谱学与光谱分析,2003, 23, 300–302.
[11] Tisza, E. T.; Duesel, B. F.; Friedman, H. L. US. 2332615, 1943–10–26.
[12] Ruben, M.; Ziener, U.; Lehn, J.-M.; Ksenofontov, V.; Gütlich, P.; Vaughan, G. B. M. Chem. Eur. J. 2005, 11, 94–100.
[13] Chi, Y.-N.; Huang, K.-L.; Cui, F.-Y.; Xu, Y.-Q.; Hu, C.-W. Inorg. Chem. 2006, 45, 10605–10612.
[14] Inagaki, A.; Yatsuda, S.; Edure, S.; Suzuki, A.; Takahashi, T.; Akita, M. Inorg. Chem. 2007, 46, 2432–2445.
[15]王建晖,硕士论文,青岛科技大学,青岛, 2009。
[16] (a) Quesada, A.; Low, J. N.; Melguizo, M.; Nogueras, M.; Glidewell, C. Acta Cryst. 2002, C58, o355–o358. (b) Quesada, A.; Marchal, A.; Melguizo, M.; Low, J. N.; Glidewell, C. Acta Cryst. 2004, B60, 76–89. (c) Quesada, A.; Marchal, A.; Melguizo, M.; Nogueras, M.; Sánchez, A.; Low, J. N.; Cannon, D.; Farrell, D. M. M.; Glidewell, C. Acta Cryst. 2002, B58, 300–315.
[17] (a) Singelenberg, F. A. J.; van Eijck, B. P. Acta Cryst. 1987, C43, 693–695. (b) Pollagi, T. P.; Geib, S. J.; Hopkins, M. D. Acta Cryst. 1994, C50, 910–913. (c)Aaker(?)y, C. B.; Schultheiss, N.; Desper, J. Inorg. Chem. 2005, 44, 4983–4991. (d) Aaker(?)y, C. B.; Schultheiss, N.; Desper, J.; Moore, C. Cryst. Growth Des. 2007, 7, 2324–2331. (e) Aaker(?)y, C. B.; Schultheiss, N.; Rajbanshi, A.; Desper, J.; Moore, C. Cryst. Growth Des. 2009, 9, 432–441.
[18] Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. 1995, 34, 1555–1573.
[19] Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104–112.
[20] (a) Price, S. L.; Stone, A. J.; Lucas, J.; Rowland, R. S.; Thornley, A. E. J. Am. Chem. Soc. 1994, 116, 4910–4918. (b) Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108–3116.
[21] Dunn, D. L.; Skinner, C. G. J. Org. Chem. 1975, 40, 3713–3716.
[22] (a) Tran, S. B.; Ekhato, I. V.; Rinehart, J. K. J. Label Compd. Radiopharm. 2009, 52, 485–489. (b) Maxwell, B. D.; Boyé, O. G.; Ohta, K. J. Label Compd. Radiopharm. 2005, 48, 397–406.
[23] Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1–S19.
[24] Garzia, A.; Bottazi, A. US. 3991190, 1976-11-09.
[25] Harris, J. M.; Neustadt, B. R.; Hao, J.-S; Stamford, A. W. WO. 2009/111449, 2008-03-04.
[26] Schirok, H.; Stasch, J.-P. WO. 2005108397, 2004-04-27.
[2] Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313?3315.
[3] Cassar, L. J. Organomet. Chem. 1975, 93, 253?257.
[4] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467?4470.
[5] (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49. (b) Tykwinski, R. R. Angew. Chem. Int. Ed. 2003, 42, 1566?1568.
[6] Plenio, H. Angew. Chem. Int. Ed. 2008, 47, 6954?6956.
[7] Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133?173.
[8] (a) Doucet, H.; Hierso, J.-C. Angew. Chem. Int. Ed. 2007, 46, 834?871. (b) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874?922. (c) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283–2321.
[9] Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551?8553.
[10] Xia, M.; Wang, Y. G. Chin. J. Org. Chem. 2003, 23, 609?612.
[11] Elangovan, A.; Wang, Y.-H.; Ho, T.-I. Org. Lett. 2003, 5, 1841?1844.
[12] Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219?224.
[13] Anastasia, L.; Negishi, E. Org. Lett. 2001, 3, 3111?3113.
[14] (a) Dai, W.-M.; Guo, D.-S.; Sun, L.-P. Tetrahedron Lett. 2001, 42, 5275–5278.
[15] Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39?46.
[16] (a) Nájera, C.; Gil-Moltó, J.; Karlstr?m, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451?1454. (b) Gil-Moltó, J.; Nájera, C. Eur. J. Org. Chem. 2005, 4073?4081.
[17] (a) Wang, R.; Piekarski, M. M.; Shreeve, J. M. Org. Biomol. Chem. 2006, 4, 1878?1886. (b) Rau, S.; Lamm, K.; G?rls, H.; Sch?ffel, J.; Walther, D. J. Organomet. Chem. 2004, 689, 3582?3592.
[18] Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411?1414.
[19] Li, J. H.; Hu, X.-C.; Liang, Y.; Xie, Y.-X. Tetrahedron 2006, 62, 31?38.
[20] Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391?393.
[21] Dibowski, H.; Schmidtchen, F. P. Tetrahedron Lett. 1998, 39, 525?528.
[22] Bleicher, L.; Cosford, N. D. P. Synlett. 1995, 1115?1116.
[23] López-Deber, M. P.; Castedo, L.; Granja, J. R. Org. Lett. 2001, 3, 2823?2826.
[24] Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron. 2001, 57, 8017?8028.
[25] Soler, R.; Cacchi, S.; Fabrizi, G.; Forte, G.; Martín, L.; Martínez, S.; Molins, E.; Moreno-Ma?as, M.; Petrucci, F.; Roig, A.; Sebastián, R. M.; Vallribera, A.Synthesis 2007, 3068?3072.
[26] Kim, J.-H.; Lee, D.-H.; Jun, B.-H.; Lee, Y.-S. Tetrahedron Lett. 2007, 48, 7079?7084.
[27] Cai, M.; Xu, Q.; Sha, J. J. Mole. Catal. A.: Chem. 2007, 272, 293?297.
[28] Cassar, L. J. Organomet. Chem. 1975, 93, 253?257.
[29] (a) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. Tetrahedron Lett. 1992, 33, 5363?5364. (b) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716?4721.
[30] Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315?4317.
[31] Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727?4729.
[32] Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843?3846.
[33] Ma, D.; Liu, F. Chem. Commun. 2004, 1934?1935.
[34] Biffis, A.; Scattolin, E.; Ravasio, N.; Zaccheria, F. Tetrahedron Lett. 2007, 48, 8761?8764.
[35] (a) Li, J.-H.; Li, J.-H.; Wang, D.-P.; Pi, S.-F.; Xie, Y.-X.; Zhang, M.-B.; Hu, X.-C. J. Org. Chem., 2007, 72, 2053?2057. (b) Tang, B.-X.; Wang, F.; Li, J.-H.; Xie, Y.-X.; Zhang, M.-B. J. Org. Chem., 2007, 72, 6294?6297.
[36] Thakur, K. G.; Jaseer, E. A.; Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2009, 50, 2865?2869.
[37] Chen, H.-J.; Lin, Z.-Y.; Li, M.-Y.; Lian, R.-J.; Xue, Q.-W.; Chung, J.-L.; Chen, S.-C.; Chen, Y.-J. Tetrahedron 2010, 66, 7755?7761.
[38] Zuidema, E.; Bolm, C. Chem. Eur. J. 2010, 16, 4181?4185.
[39] Beletskaya, I. P.; Latyshev, G. V.; Tsvetkov, A. V.; Lukashev, N. V. Tetrahedron Lett. 2003, 44, 5011?5013.
[40] Wang, L.; Li, P.; Zhang, Y. Chem. Commun. 2004, 514?515.
[41] de Souza, R. O. M. A.; Bittar, M. S.; Mendes, L. V. P.; da Silva, C. M. F.; da Silva, V. T.; Antunes, O. A. C. Synlett. 2008, 1777?1780.
[42] González-Arellano, C.; Abad, A.; Corma, A.; García, H.; Iglesias, M.; Sánchez, F.Angew. Chem. Int. Ed. 2007, 46, 1536?1538.
[43] Li, P.; Wang, L.; Wang, M.; You, F. Eur. J. Org. Chem. 2008, 5946?5951.
[44] Park, S.; Kim. M.; Koo, D. H.; Chang, S. Adv. Synth. Catal. 2004, 346, 1638?1640.
[45] For general reviews, see: (a) Correa, A.; Manche?o, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108?1117. (b) Enthaler, S.; Junge, K.; Beller, M. Angew. Chem. Int. Ed. 2008, 47, 3317?3321. (c) Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500?1511. (d) Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624?629. (e) Bolm, C., Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217?6254.
[46] (a) Cahiez, G.; Foulgoc, L.; Moyeux, A. Angew. Chem. Int. Ed. 2009, 48, 2969?2972. (b) Volla, C. M. R.; Vogel, P. Angew. Chem. Int. Ed. 2008, 47, 1305?1307. (c) Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844?9845. (d) Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J. Org. Lett. 2005, 7, 1219?1222. (e) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856?13863.
[47] (a) Correa, A.; Carril, M.; Bolm, C. Angew. Chem. Int. Ed. 2008, 47, 2880?2883. (b) Correa, A.; Carril, M.; Bolm, C. Chem. Eur. J. 2008, 14, 10919?10922. (c) Mayer, A. C.; Salit, A.-F.; Bolm, C. Chem. Commun. 2008, 5975?5977. (d) Correa, A.; Bolm, C. Adv. Synth. Catal. 2008, 350, 391?394.
[48] Carril, M.; Correa, A.; Bolm, C. Angew. Chem. Int. Ed. 2008, 47, 4862?4865.
[49] Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2008, 73, 9061?9064.
[50] Volla, C. M. R.; Vogel, P. Tetrahedron Lett. 2008, 49, 5961?5964.
[51] Sawant, D. N.; Tambade, P. J.; Wagh, Y. S.; Bhanage, B. M. Tetrahedron Lett. 2010, 51, 2758?2761.
[52] Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176?4211.
[53] Sakamoto, T.; Shiraiwa, M.; Kondo, Y.; Yamanaka, H. Synthesis 1983, 312?314.
[54] Ames, D. E.; Brohi, M. I. J. Chem. Soc. Perkins. Trans. 1 1980, 1384?1389.
[55] Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818?819.
[56] Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127?14136.
[57] K?llhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem. Int. Ed. 2003, 42, 1056?1058.
[58] Remmele, H.; K?llhofer, A.; Plenio, H. Organometallics 2003, 22, 4098?4103.
[59] Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 42, 5993?5996.
[60] Anderson, K. W.; Buchwald, S. L. Angew. Chem. 2005, 117, 6329?6333.
[61] Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2004, 45, 8443–8446.
[62] Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P. Org. Lett. 2004, 6, 3473?3476.
[63] Yi, C.; Hua, R. J. Org. Chem. 2006, 71, 2535?2537.
[64] Komáromi, A.; Novák, Z. Chem. Commun. 2008, 4968?4970.
[65] Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem. 2008, 73, 6037?6040.
[66] Torborg, C.; Huang, J.; Schulz, T.; Sch?ffner, B.; Zapf, A.; Spannenberg, A.; B?rner, A.; Beller, M. Chem. Eur. J. 2009, 15, 1329?1336.
[67] Jin, M.-J.; Lee, D.-H. Angew. Chem. Int. Ed. 2010, 49, 1119?1122.
[1] (a) Daiber, A.; Oelze, M.; Coldewey, M.; Kaiser, K.; Huth, C.; Schildknecht, S.; Bachschmid, M.; Nazirisadeh, Y.; Ullrich, V.; Mülsch, A.; Münzel, T.; Tsilimingas, N. Biochem. Biophys. Res. Commun. 2005, 338, 1865–1874. (b) Bang, L.; Nielsen-Kudsk, J. E.; Gruhn, N.; Trautner, S.; Theilgaard, S. A.; Olesen, S.-P.; Boesgaard, S.; Aldershvile, J. Eur. J. Pharmacol. 1998, 361, 43–49.
[2] (a) Steyn, D. W.; Odendaal, H. J. Eur. J. Obstet. Gynecol. Reprod. Biol. 1997, 75, 155–159. (b) Wacker, J. R.; Wagner, B. K.; Briese, V.; Schauf, B.; Heilmann, L.; Bartz, C.; Hopp, H. Eur. J. Obstet. Gynecol. Reprod. Biol. 2006, 127, 160–165.
[3] (a) Gasiorowski, K.; Szyba, K.; Wozniak, D.; Gulanowski, B. Mutagenesis 1997, 12, 411–415. (b) Gasiorowski, K.; Brokos, B. Mutagenesis 2000, 15, 137–141.
[4] Saito, H.; Minami, M. Antihypertensive drugs today Ed. Saito, H. Koninklijke W?hrmann BV, The Netherlands, 1991.
[5] Piatnitski, E. L.; Duncton, M. A. J.; Kiselyov, A. S.; Katoch-Rouse, R.; Sherman, D.; Milligan, D. L.; Balagtas, C.; Wong, W. C.; Kawakami, J.; Doody, J. F. Bioorg. Med. Chem. Lett. 2005, 15, 4696–4698.
[6] Madhavan, G. R.; Chakrabarti, R.; Kumar, S. K. B.; Misra, P.; Mamidi, R. N. V. S.; Balraju, V.; Kasiram, K.; Babu, R. K.; Suresh, J.; Lohray, B. B.; Lohrayb, V. B.; Iqbal, J.; Rajagopalan, R. Eur. J. Med. Chem. 2001, 36, 627–637.
[7] Rodríguez-Ciria, M.; Sanz, A. M.; Yunta, M. J. R.; Gomez-Contreras, F.; Navarro, P.; Fernandez, I.; Pardo M.; Cano, C. Bioorg. Med. Chem. 2003, 11, 2143–2148.
[8]林国强,刘汉泉,杨细文,CN. 1523024A,2004–08–25.
[9] Chen, L.; Thompson, L. K.; Tandon, S. S.; Bridson, J. N. Inorg. Chem. 1993, 32, 4063–4068.
[10] Deng, Z.; Tseng, H.-W.; Zong, R.; Wang, D.; Thummel, R. Inorg. Chem. 2008, 47, 1835–1848.
[11] Barrios, A. M.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 11751–11757.
[12] (a) Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133–173. (b) Seki, M. Synthesis 2006, 2975–2992.
[13] (a) Sullivan, D. A.; Palenik, G. J. Inorg. Chem. 1997, 16, 1127–1133. (b) Okabe, N.; Fukuda, H.; Nakamura, T. Acta Cryst. 1993, C49, 1844–1845. (c) Kuzelka, J.; Mukhopadhyay, S.; Spingler, B.; Lippard, S. J. Inorg. Chem. 2004, 43, 1751?1761. (d) Barrios, A. M.; Lippard, S. J. Inorg. Chem. 2001, 40, 1060–1064. (e) Kuzelka, J.; Spingler, B.; Lippard, S. J. Inorg. Chim. Acta 2002, 337, 212–222.
[14] (a) Singelenberg, F. A. J.; van Eijck, B. P. Acta Cryst. 1987, C43, 693–695. (b) Pollagi, T. P.; Geib, S. J.; Hopkins, M. D. Acta Cryst. 1994, C50, 910–913. (c) Aaker?y, C. B.; Schultheiss, N.; Desper, J. Inorg. Chem. 2005, 44, 4983–4991. (d) Aaker?y, C. B.; Schultheiss, N.; Desper, J.; Moore, C. Cryst. Growth Des. 2007, 7, 2324–2331. (e) Aaker?y, C. B.; Schultheiss, N.; Rajbanshi, A.; Desper, J.; Moore, C. Cryst. Growth Des. 2009, 9, 432–441.
[15] Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. 1995, 34, 1555–1573.
[16] Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104–112.
[17] Sivakumar, R.; Gnanasam, S. K.; Ramachandran, S.; Leonard, J. T. Eur. J. Med. Chem. 2002, 37, 793–801.
[18]李学华,涂光忠,安东各,合成化学,2005, 13, 204–205.
[1] Gangjee, A.; Shi, J.; Queener, S. F. J. Med. Chem. 1997, 40, 1930–1936.
[2] Herbrecht, R.; Denning, D. W.; Patterson, T. F.; Bennett, J. E.; Greene, R. E.; Oestmann, J.-W.; Kern, W. V.; Marr, K. A. N. Engl. J. Med. 2002, 347, 408–415.
[3] (a) Gangjee, A.; Lin, X.; Kisliuk, R. L.; McGuire, J. J. J. Med. Chem. 2005, 48,7215–7222. (b) Gangjee, A.; Li, W.; Yang, J.; Kisliuk, R. L. J. Med. Chem. 2008, 51, 68–76.
[4]祁雪丹,屠树滋,王秋娟,中国新药杂志,2003, 12, 810–816.
[5]希尔艾力?买买提依明,硕士论文,新疆大学,乌鲁木齐,2008.
[6] (a) Levitt, G.; Baker, D. Synthesis and chemistry of agrochemicals II 1991, 16–31. (b)范志金,刘丰茂,钱传范,农药,1999, 38, 6–9.
[7] (a) Deng, F.; Hatzios, K. K. Pestic. Biochem. Phys. 2003, 74, 102–115. (b) Milliman, L. D.; Riechers, D. E.; Wax, L. M.; Simmons, F. W. Weed Sci. 2003, 51, 139–144. (c) Lun, A. F.; Chikoye, D.; Adesiyan, S. O. Weed Technol. 2005, 19, 122–127.
[8] Tamaru, M.; Saito, Y. Pestic. Sci. 1996, 47, 125–130.
[9] (a) Tamaru, M.; Takehi, T.; Masuyama, N. Pestic. Sci. 1996, 47, 327–335. (b) Nezu, Y.; Miyazaki, M.; Sugiyama, K.; Kajiwara, I. Pestic. Sci. 1996, 47, 103–113.
[10]魏青,李丽,高胜利,光谱学与光谱分析,2003, 23, 300–302.
[11] Tisza, E. T.; Duesel, B. F.; Friedman, H. L. US. 2332615, 1943–10–26.
[12] Ruben, M.; Ziener, U.; Lehn, J.-M.; Ksenofontov, V.; Gütlich, P.; Vaughan, G. B. M. Chem. Eur. J. 2005, 11, 94–100.
[13] Chi, Y.-N.; Huang, K.-L.; Cui, F.-Y.; Xu, Y.-Q.; Hu, C.-W. Inorg. Chem. 2006, 45, 10605–10612.
[14] Inagaki, A.; Yatsuda, S.; Edure, S.; Suzuki, A.; Takahashi, T.; Akita, M. Inorg. Chem. 2007, 46, 2432–2445.
[15]王建晖,硕士论文,青岛科技大学,青岛, 2009。
[16] (a) Quesada, A.; Low, J. N.; Melguizo, M.; Nogueras, M.; Glidewell, C. Acta Cryst. 2002, C58, o355–o358. (b) Quesada, A.; Marchal, A.; Melguizo, M.; Low, J. N.; Glidewell, C. Acta Cryst. 2004, B60, 76–89. (c) Quesada, A.; Marchal, A.; Melguizo, M.; Nogueras, M.; Sánchez, A.; Low, J. N.; Cannon, D.; Farrell, D. M. M.; Glidewell, C. Acta Cryst. 2002, B58, 300–315.
[17] (a) Singelenberg, F. A. J.; van Eijck, B. P. Acta Cryst. 1987, C43, 693–695. (b) Pollagi, T. P.; Geib, S. J.; Hopkins, M. D. Acta Cryst. 1994, C50, 910–913. (c)Aaker(?)y, C. B.; Schultheiss, N.; Desper, J. Inorg. Chem. 2005, 44, 4983–4991. (d) Aaker(?)y, C. B.; Schultheiss, N.; Desper, J.; Moore, C. Cryst. Growth Des. 2007, 7, 2324–2331. (e) Aaker(?)y, C. B.; Schultheiss, N.; Rajbanshi, A.; Desper, J.; Moore, C. Cryst. Growth Des. 2009, 9, 432–441.
[18] Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. 1995, 34, 1555–1573.
[19] Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104–112.
[20] (a) Price, S. L.; Stone, A. J.; Lucas, J.; Rowland, R. S.; Thornley, A. E. J. Am. Chem. Soc. 1994, 116, 4910–4918. (b) Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108–3116.
[21] Dunn, D. L.; Skinner, C. G. J. Org. Chem. 1975, 40, 3713–3716.
[22] (a) Tran, S. B.; Ekhato, I. V.; Rinehart, J. K. J. Label Compd. Radiopharm. 2009, 52, 485–489. (b) Maxwell, B. D.; Boyé, O. G.; Ohta, K. J. Label Compd. Radiopharm. 2005, 48, 397–406.
[23] Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1–S19.
[24] Garzia, A.; Bottazi, A. US. 3991190, 1976-11-09.
[25] Harris, J. M.; Neustadt, B. R.; Hao, J.-S; Stamford, A. W. WO. 2009/111449, 2008-03-04.
[26] Schirok, H.; Stasch, J.-P. WO. 2005108397, 2004-04-27.
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