Hofmann重排反应的应用进展
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摘要
介绍了Hofmann重排反应法的特点及机理,总结了酰胺Hofmann重排反应法制备胺、氨基甲酸酯、脲等化合物的应用进展,及反应所用的试剂等反应条件。指出应加强对Hofmann重排反应的系统性研究,及近年国外报道较多的高价碘试剂诱导的Hofmann重排反应。
This review introduced the characteristics and mechanism of Hofmann rearrangement reaction,summarized the application advances of amide Hofmann rearrangement reaction in preparing organic compounds such as amines,carbamate,ureas etc,and pointed the reaction conditions such as reagents.Systematic research on Hofmann rearrangements reaction should be strengthened and emphasized on Hofmann rearrangement reaction induced by novel hyervalent iodine reagent.
This review introduced the characteristics and mechanism of Hofmann rearrangement reaction,summarized the application advances of amide Hofmann rearrangement reaction in preparing organic compounds such as amines,carbamate,ureas etc,and pointed the reaction conditions such as reagents.Systematic research on Hofmann rearrangements reaction should be strengthened and emphasized on Hofmann rearrangement reaction induced by novel hyervalent iodine reagent.
引文
[1]闻韧.药物合成反应[M].2版.北京:化学工业出版社,2003:253-256.
[2]黄宪,王彦广,陈振初.新编有机合成化学[M].2版.北京:化学工业出版社,2003:606-608.
[3]李德江,孙碧海,李斌.浅谈Hofmann重排反应在有机合成中的应用[J].化学教育,2006(4):4-5.
[4]蔡亚,汪斌,高正兵,等.对羟基苯乙胺盐酸盐的合成[J].应用化工,2009,38(5):763-765.
[5]杨健,黄燕.普瑞巴林的合成[J].高校化学工程学报,2009,23(5):825-829.
[6]龚美义.普瑞巴林的合成[J].广东化工,2009,36(5):129-130.
[7]张桂森,杨相平,刘笔锋.普瑞巴林的合成[J].中国医药工业杂志,2007,38(9):617-618.
[8]钟为慧,江灵波,陈霄,等.卡比多巴的合成[J].中国医药工业杂志,2008,39(10):730-732.
[9]杨智勇.卡比多巴合成工艺的研究[J].化学工程与装备,2007(3):27-31.
[10]朱建明.正交设计优化帕珠沙星Hofmann重排反应工艺[J].中国药师,2007,10(3):249-250.
[11]智翠梅,温艳珍,王齐.甲磺酸帕珠沙星的合成[J].应用化工,2007,36(5):472-474.
[12]刘艳飞,黄可龙,彭东明,等.甲磺酸帕珠沙星的合成工艺改进[J].中国药物化学杂志,2005,15(6):344-346,350.
[13]钱方,黎文海.甲磺酸帕珠沙星的合成[J].山西化工,2011,31(3):7-9,34.
[14]申绪湘,彭晓春,龚兴浪,等.抗菌药甲磺酸帕珠沙星的合成[J].吉首大学学报:自然科学版,2009,30(5):96-100.
[15]李建华,钟静芬,时惠麟.群多普利的合成[J].中国医药工业杂志,2007,38(7):465-467.
[16]周庆江,黄山.巴洛沙星中间体3-甲氨基哌啶二盐酸盐的合成[J].山西化工,2008,28(5):11-13.
[17]谭红梅,马玉卓.4-氨基-4-甲基吡啶二对甲苯磺酸盐的合成[J].广东药学院学报,2011,27(3):247-249.
[18]杨维成,齐庆瑞,刘卫霞,等.稳定同位素标记15 N-N,N-二甲基苯胺的合成[J].有机化学,2012,32:145-148.
[19]邢孔强,刘煜,朱美香,等.4-溴-N,N-二(4-叔丁基苯基)-苯胺的合成及其光谱性能的研究[J].湘潭大学自然科学学报,2006,28(3):64-67.
[20]张福乾,陈宏博.霍夫曼降解反应制备3,5-二甲基苯胺及反应动力学研究[J].辽东学院学报:自然科学版,2010,17(1):8-13,17.
[21]姜艳,孟启,席海涛,等.2-硝基-3-氯苯胺的合成[J].精细石油化工,2005(4):8-9.
[22]田志高,刘安昌,谭珍友,等.3-硝基-2-氨基苯甲酸的合成[J].合成化学,2009,17(1):106-108.
[23]沈超,王慧源,柳军,等.苯并咪唑类聚腺苷二磷酸核糖聚合酶抑制剂的合成及初步活性研究[J].中国药物化学杂志,2011,21(2):106-112.
[24]黄斌,宋丽艳,余文学,等.2,6-二氟苯胺的合成[J].江西化工,2006(1):83-84.
[25]熊国兰,蒋柏泉,赖晓波.高效杀虫剂原料2,6-二氟苯胺合成工艺的研究[J].安徽农业科学,2008,36(23):9848-9849.
[26]何光文,陈宏博,王伟杰.2,3,5,6-四氟苯胺的合成[J].精细化工中间体,2008,38(2):40-41.
[27]魏科年,单玉华,李为民,等.对苯二胺合成新工艺的研究[J].石油化工,2005,34(2):157-159.
[28]戴立言,方俊,王晓钟,等.Synthesis of2-pyridinamines and their alkyl derivatives from2-cyanopyridines[J].化工学报,2007,58(3):670-672.
[29]穆飞虎,魏运洋,刘霖.3-甲氨基哌啶二盐酸盐的合成[J].化学试剂,2007,29(9):557-558.
[30]阙丹华,李玉峰,左杭冬,等.2-氯-3-三氟乙氧基吡啶的合成[J].精细化工中间体,2010,40(4):24-26.
[31]龚红烈,陈印川,邸文平,等.2,3-二氯吡啶合成方法的研究[J].河北化工,2011,34(1):57-59.
[32]苏策,张凯明,贺俊华.2-氨基烟酸的合成[J].化工学报,2011,62(2):580-583.
[33]肖庆,刘安昌,谭珍友,等.2-氯-3-氨基-4-甲基吡啶的合成[J].武汉工程大学学报,2008,30(4):33-35.
[34]方永勤,孙德鑫,许亮,等.2-氨基-6-溴吡啶的合成研究[J].化学世界,2010(6):346-348.
[35]李晓娟,戴立言,王晓钟,等.2-氨基-3-甲基吡啶的合成新方法[J].化学世界,2006(2):105-107.
[36]苏策,贺俊华.4-氨基烟酸的合成研究[J].高校化学工程学报,2010,24(5):907-910.
[37]孟庆伟,曾伟,赖琼,等.奈韦拉平的合成[J].中国医药工业杂志,2006,37(1):5-7.
[38]陶晓璇,郑志兵,陈伟,等.1-(5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-基)-3-(吡啶-3-基甲基)脲的合成[J].化学试剂,2012,34(7):581-584.
[39]梁长玉,胡炳成,戴红升,等.一种简易合成3,5-二氨基吡啶的方法[J].含能材料,2011,19(5):513-517.
[40]胡炳成,梁长玉,陆明,等.一种合成3,5-二氨基吡啶及3,5-二甲基羰基氨基吡啶的新路线[J].应用化学,2012,29(1):80-83.
[41]Gogoi P,Konwar D.An efficient modification of the Hofmann rearrangement:synthesis of methyl carbamates[J].Tetrahedron Lett,2007,48:531-533.
[42]Borah A J,Phukan P.Efficient synthesis of methyl carbamate via Hofmann rearrangement in the presence of TsNBr 2[J].Tetrahedron Lett,2012,53:3035-3037.
[43]Zhang Y,Lin C,Li Z,et al.Synthesis of[15N]t-butylamine hydrochloride[J].J Label Compd Radiopharm,2010,53:183-185.
[44]Yoshimura A,Luedtke M W,Zhdankin V V.(Tosylimino)phenyl-λ3-iodane as a reagent for the synthesis of methyl carbamates via Hofmann rearrangement of aromatic and aliphatic carboxamides[J].J Org Chem,2012,77:2087-2091.
[45]Palmer A M,Munch G,Scheufler C,et al.Synthesis and pharmacological evaluation of5-carboxamide-substituted tetrahydro-chromeno[7,8-d]imidazoles[J].Tetrahedron Lett,2009,50:3920-3922.
[46]Landsberg D,Kalesse M.Synthesis of Symmetrical Ureas by(Diacetoxy-iodo)benzene-InducedHofmannRearrangement[J].Synlett.2010(7):1104-1106.
[47]Angelici G,Contaldi S,Green S L,et al.Synthesis of imidazolidin-2-one-4-carboxylate and of(te trahydro)pyrimidin-2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement[J].Org Biomol Chem,2008,6:1849-1852.
[48]Deady L W,Devine S M.Novel annulated prod ucts from aminonaphthyridinones[J].Tetrahedron,2006,62:2313-2320.
[49]Okamoto N,Miwa Y,Minami H,et al.Concise One-Pot Tandem Synthesis of Indoles and Isoquinolines from Amides[J].Angew Chem Int Ed Engl,2009,48:9693-9696.
[50]Song H,Chen W,Wang Y,et al.Preparation of alkyl carbamate of1-protected indole-3-methylamine as a precursor of indole-3-methylamine[J].Synth Commun,2005,35:2735-2748.
[51]Hernandez E,Velez J M,Vlaar C P.Synthesis of1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol[J].Tetrahedron Lett,2007,48:8972-8975.
[52]Lau Y H,Spring D R.Efficient Synthesis of Fmoc-Protected Azido Amino Acids[J].Synlett,2011,13:1917-1919.
[53]Liu S J,Zhang J Z,Tian G R,et al.Synthesis of Alkyla-mmonium Tosylates with Poly{[4-Hydroxy(Tosyloxy)Iodo]Styrene}[J].Synth Commun,2005,35:823-827.
[54]Liu P,Wang Z,Hu X.Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced Hofmann rearrangement[J].Eur J Org Chem,2012:1994-2000.
[55]Miyamoto K,Sakai Y,Goda S,et al.A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides:Iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant[J].Chem Commun,2012,48:982-984.
[56]Moriyama K,Ishida K,Togo H.Hofmann-type rearrangementof imides by in situ generation of imide-hypervalent iodines(III)from iodoarenes[J].Org Lett,2012,14:946-949.
[57]Zagulyaeva A A,Banek C T,Yusubov M S,et al.Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone:Reaction scope and limitations[J].Org Lett,2010,12:4644-4647.
[2]黄宪,王彦广,陈振初.新编有机合成化学[M].2版.北京:化学工业出版社,2003:606-608.
[3]李德江,孙碧海,李斌.浅谈Hofmann重排反应在有机合成中的应用[J].化学教育,2006(4):4-5.
[4]蔡亚,汪斌,高正兵,等.对羟基苯乙胺盐酸盐的合成[J].应用化工,2009,38(5):763-765.
[5]杨健,黄燕.普瑞巴林的合成[J].高校化学工程学报,2009,23(5):825-829.
[6]龚美义.普瑞巴林的合成[J].广东化工,2009,36(5):129-130.
[7]张桂森,杨相平,刘笔锋.普瑞巴林的合成[J].中国医药工业杂志,2007,38(9):617-618.
[8]钟为慧,江灵波,陈霄,等.卡比多巴的合成[J].中国医药工业杂志,2008,39(10):730-732.
[9]杨智勇.卡比多巴合成工艺的研究[J].化学工程与装备,2007(3):27-31.
[10]朱建明.正交设计优化帕珠沙星Hofmann重排反应工艺[J].中国药师,2007,10(3):249-250.
[11]智翠梅,温艳珍,王齐.甲磺酸帕珠沙星的合成[J].应用化工,2007,36(5):472-474.
[12]刘艳飞,黄可龙,彭东明,等.甲磺酸帕珠沙星的合成工艺改进[J].中国药物化学杂志,2005,15(6):344-346,350.
[13]钱方,黎文海.甲磺酸帕珠沙星的合成[J].山西化工,2011,31(3):7-9,34.
[14]申绪湘,彭晓春,龚兴浪,等.抗菌药甲磺酸帕珠沙星的合成[J].吉首大学学报:自然科学版,2009,30(5):96-100.
[15]李建华,钟静芬,时惠麟.群多普利的合成[J].中国医药工业杂志,2007,38(7):465-467.
[16]周庆江,黄山.巴洛沙星中间体3-甲氨基哌啶二盐酸盐的合成[J].山西化工,2008,28(5):11-13.
[17]谭红梅,马玉卓.4-氨基-4-甲基吡啶二对甲苯磺酸盐的合成[J].广东药学院学报,2011,27(3):247-249.
[18]杨维成,齐庆瑞,刘卫霞,等.稳定同位素标记15 N-N,N-二甲基苯胺的合成[J].有机化学,2012,32:145-148.
[19]邢孔强,刘煜,朱美香,等.4-溴-N,N-二(4-叔丁基苯基)-苯胺的合成及其光谱性能的研究[J].湘潭大学自然科学学报,2006,28(3):64-67.
[20]张福乾,陈宏博.霍夫曼降解反应制备3,5-二甲基苯胺及反应动力学研究[J].辽东学院学报:自然科学版,2010,17(1):8-13,17.
[21]姜艳,孟启,席海涛,等.2-硝基-3-氯苯胺的合成[J].精细石油化工,2005(4):8-9.
[22]田志高,刘安昌,谭珍友,等.3-硝基-2-氨基苯甲酸的合成[J].合成化学,2009,17(1):106-108.
[23]沈超,王慧源,柳军,等.苯并咪唑类聚腺苷二磷酸核糖聚合酶抑制剂的合成及初步活性研究[J].中国药物化学杂志,2011,21(2):106-112.
[24]黄斌,宋丽艳,余文学,等.2,6-二氟苯胺的合成[J].江西化工,2006(1):83-84.
[25]熊国兰,蒋柏泉,赖晓波.高效杀虫剂原料2,6-二氟苯胺合成工艺的研究[J].安徽农业科学,2008,36(23):9848-9849.
[26]何光文,陈宏博,王伟杰.2,3,5,6-四氟苯胺的合成[J].精细化工中间体,2008,38(2):40-41.
[27]魏科年,单玉华,李为民,等.对苯二胺合成新工艺的研究[J].石油化工,2005,34(2):157-159.
[28]戴立言,方俊,王晓钟,等.Synthesis of2-pyridinamines and their alkyl derivatives from2-cyanopyridines[J].化工学报,2007,58(3):670-672.
[29]穆飞虎,魏运洋,刘霖.3-甲氨基哌啶二盐酸盐的合成[J].化学试剂,2007,29(9):557-558.
[30]阙丹华,李玉峰,左杭冬,等.2-氯-3-三氟乙氧基吡啶的合成[J].精细化工中间体,2010,40(4):24-26.
[31]龚红烈,陈印川,邸文平,等.2,3-二氯吡啶合成方法的研究[J].河北化工,2011,34(1):57-59.
[32]苏策,张凯明,贺俊华.2-氨基烟酸的合成[J].化工学报,2011,62(2):580-583.
[33]肖庆,刘安昌,谭珍友,等.2-氯-3-氨基-4-甲基吡啶的合成[J].武汉工程大学学报,2008,30(4):33-35.
[34]方永勤,孙德鑫,许亮,等.2-氨基-6-溴吡啶的合成研究[J].化学世界,2010(6):346-348.
[35]李晓娟,戴立言,王晓钟,等.2-氨基-3-甲基吡啶的合成新方法[J].化学世界,2006(2):105-107.
[36]苏策,贺俊华.4-氨基烟酸的合成研究[J].高校化学工程学报,2010,24(5):907-910.
[37]孟庆伟,曾伟,赖琼,等.奈韦拉平的合成[J].中国医药工业杂志,2006,37(1):5-7.
[38]陶晓璇,郑志兵,陈伟,等.1-(5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-基)-3-(吡啶-3-基甲基)脲的合成[J].化学试剂,2012,34(7):581-584.
[39]梁长玉,胡炳成,戴红升,等.一种简易合成3,5-二氨基吡啶的方法[J].含能材料,2011,19(5):513-517.
[40]胡炳成,梁长玉,陆明,等.一种合成3,5-二氨基吡啶及3,5-二甲基羰基氨基吡啶的新路线[J].应用化学,2012,29(1):80-83.
[41]Gogoi P,Konwar D.An efficient modification of the Hofmann rearrangement:synthesis of methyl carbamates[J].Tetrahedron Lett,2007,48:531-533.
[42]Borah A J,Phukan P.Efficient synthesis of methyl carbamate via Hofmann rearrangement in the presence of TsNBr 2[J].Tetrahedron Lett,2012,53:3035-3037.
[43]Zhang Y,Lin C,Li Z,et al.Synthesis of[15N]t-butylamine hydrochloride[J].J Label Compd Radiopharm,2010,53:183-185.
[44]Yoshimura A,Luedtke M W,Zhdankin V V.(Tosylimino)phenyl-λ3-iodane as a reagent for the synthesis of methyl carbamates via Hofmann rearrangement of aromatic and aliphatic carboxamides[J].J Org Chem,2012,77:2087-2091.
[45]Palmer A M,Munch G,Scheufler C,et al.Synthesis and pharmacological evaluation of5-carboxamide-substituted tetrahydro-chromeno[7,8-d]imidazoles[J].Tetrahedron Lett,2009,50:3920-3922.
[46]Landsberg D,Kalesse M.Synthesis of Symmetrical Ureas by(Diacetoxy-iodo)benzene-InducedHofmannRearrangement[J].Synlett.2010(7):1104-1106.
[47]Angelici G,Contaldi S,Green S L,et al.Synthesis of imidazolidin-2-one-4-carboxylate and of(te trahydro)pyrimidin-2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement[J].Org Biomol Chem,2008,6:1849-1852.
[48]Deady L W,Devine S M.Novel annulated prod ucts from aminonaphthyridinones[J].Tetrahedron,2006,62:2313-2320.
[49]Okamoto N,Miwa Y,Minami H,et al.Concise One-Pot Tandem Synthesis of Indoles and Isoquinolines from Amides[J].Angew Chem Int Ed Engl,2009,48:9693-9696.
[50]Song H,Chen W,Wang Y,et al.Preparation of alkyl carbamate of1-protected indole-3-methylamine as a precursor of indole-3-methylamine[J].Synth Commun,2005,35:2735-2748.
[51]Hernandez E,Velez J M,Vlaar C P.Synthesis of1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol[J].Tetrahedron Lett,2007,48:8972-8975.
[52]Lau Y H,Spring D R.Efficient Synthesis of Fmoc-Protected Azido Amino Acids[J].Synlett,2011,13:1917-1919.
[53]Liu S J,Zhang J Z,Tian G R,et al.Synthesis of Alkyla-mmonium Tosylates with Poly{[4-Hydroxy(Tosyloxy)Iodo]Styrene}[J].Synth Commun,2005,35:823-827.
[54]Liu P,Wang Z,Hu X.Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced Hofmann rearrangement[J].Eur J Org Chem,2012:1994-2000.
[55]Miyamoto K,Sakai Y,Goda S,et al.A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides:Iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant[J].Chem Commun,2012,48:982-984.
[56]Moriyama K,Ishida K,Togo H.Hofmann-type rearrangementof imides by in situ generation of imide-hypervalent iodines(III)from iodoarenes[J].Org Lett,2012,14:946-949.
[57]Zagulyaeva A A,Banek C T,Yusubov M S,et al.Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone:Reaction scope and limitations[J].Org Lett,2010,12:4644-4647.