Synthesis and structural investigation of new isothiochromen-4-one 2,2-dioxide derivatives

详细信息    查看全文

• 作者：Olena O. Shyshkina ; Volodymyr V. Medviediev ; Yulian M. Volovenko…
• 关键词：Isothiochromen ; 4 ; one 2 ; 2 ; dioxide ; Derivatives ; Electrophilic substitution reactions ; Tautomerism ; X ; ray diffraction
• 刊名：Structural Chemistry
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：27
• 期：1
• 页码：273-280
• 全文大小：1,044 KB
• 参考文献：1.Peixoto Ch, Laurin P, Klich M, Dupuis-Hamelin C, Mauvais P, Lassaigne P, Bonnefoy A, Musicki B (2000) Tetrahedron Lett 41:1741–1745CrossRef
  2.Pfizer Incorporation (1972) US Patent 1259415; Chem. Abstr. (1972) 76:92907
  3.Toshima K, Ohta K, Ohtasuka A, Matsumura Sh, Nakata M (1993) J Chem Soc, Chem Commun 18:1406–1407CrossRef
  4.Sohda T, Tsuda M, Yamazaki I (1991) US Patent 5071841; Chem. Abstr. (1991) 114:23804
  5.Ohta T, Komoriya S, Yoshino T, Uoto K, Nokomoto Y, Naito H, Mochizuki A, Nagata T, Kanno H, Haginoya N, Yoshikawa K, Nagamochi M, Kobayashi S (2004) Ono M (2004) EP 1405852. Chem. Abstr. 138:73271
  6.John V, Maillard M, Fang L, Tucker J, Brogley L, Aquino J, Bowers J, Probst G, Tung J (2005) Patent WO 2005/087714; Chem. Abstr. (2005) 143:326226
  7.Zhu Q, Fang L, Zhang G (2000) Zhongguo Yaowu Huaxue Zazhi. 10:1–4
  8.Dey D, Neogi P, Sen A, Sharma SD, Nag B (2002) Patent WO 02/30888; Chem. Abstr. (2002) 136:309858
  9.Krishna MV, Ramadas SR (1981) Heterocycles 16:405–409CrossRef
  10.Ramadas SR, Chenchaiah C (1981) Steroids 37:353–359CrossRef
  11.Terasawa T, Okada T (1979) J. Chem. Soc Perkin Trans 1:990–1003CrossRef
  12.Reddy NS, Reddy EP, Reddy MVR (2004) Synth. Commun. 34:2691–2695
  13.Pulman DA, Whiting DA (1973) J. Chem. Soc., Perkin Trans. 1:410–418CrossRef
  14.Simpkins NS (1993) Sulfones in organic synthesis. Pergamon Press, Oxford
  15.Shyshkina OO, Tkachuk TM, Volovnenko TA, Volovenko YuM, Zubatyuk RI, Medviediev VV, Shishkin OV (2012) Tetrahedron Lett 53:4296–4299CrossRef
  16.Tkachuk TM, Shyshkina OO, Volovnenko TA, Volovenko YuM, Zubatyuk RI, Medviediev VV, Shishkin OV (2013) Monatsh Chem 144:263–271CrossRef
  17.Shyshkina OO, Medviediev VV, Shishkin OV, Kysil AI, Volovenko YuM (2015) Tetrahedron 71:1283–1286CrossRef
  18.Pouchert CJ (1985) The Aldrich library of FT-IR spectra, Edition 1. Milwaukee (Wisconsin), Aldrich chemical comp
  19.Sheldrick G (2008) Acta Cryst Sect. A. 64:112–122CrossRef
  
• 作者单位：Olena O. Shyshkina (1)
  Volodymyr V. Medviediev (2)
  Yulian M. Volovenko (1)
  Oleg V. Shishkin (2) (3)
  
  1. Department of Chemistry, Taras Shevchenko National University of Kyiv, Lva Tolstoho Street, 12, Kyiv, 01033, Ukraine
  2. SSI “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Nauky ave., Kharkiv, 61001, Ukraine
  3. Department of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq, Kharkiv, 61122, Ukraine
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Physical Chemistry
  Theoretical and Computational Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-9001

文摘

This article presents a combined experimental and computational study of novel isothiochromene 2,2-dioxide derivatives, which were synthesized by the electrophilic substitution reactions. The compounds have been studied by NMR, IR spectroscopy and single-crystal X-ray analysis. According to X-ray diffraction data, the six-membered ring of 6 adopts a distorted half-chair conformation, but in case of compounds 7 and 8, we have a twist-boat conformation of the six-membered ring with deviation of the S1 and C8 atoms from the mean plane of the remaining atoms of the ring, respectively. Results of quantum-chemical calculations of possible isomers and tautomers of the isolated oxime 8 and azo compounds 10 at the B3LYP/aug-cc-pVDZ level indicate that the oxime-oxo tautomer (8a) is more stable than the nitroso-hydroxy tautomer (8b) in agreement with the crystal data and that the keto tautomer (II) is more stable than the hydroxyl tautomer (I) and zwitterion tautomer (III), because of a strong intramolecular hydrogen bond N–H···O. Keywords Isothiochromen-4-one 2,2-dioxide Derivatives Electrophilic substitution reactions Tautomerism X-ray diffraction