1-ARYL-4-(2-OXOALKYLSULFANYL)-2,3(5<i>H</i>)-BENZODIAZEPINES: SYNTHESIS AND THIOPHENE RING ANNULATION TO 1,2-DIAZEPINE CORE

Authors

  • Natalia M. Bohdan Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Diana S. Stepanova Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Serhii Yu. Suikov Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Vadim Yu. Popov L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 50 Kharkivs'ke Road, Kyiv 02155, Ukraine
  • Yuri V. Ishkov I. I. Mechnikov Odesa National University, 2 Dvoryanskaya St., Odesa 65082, Ukraine
  • Serhii L. Bohza Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 50 Kharkivs'ke Road, Kyiv 02155, Ukraine

DOI:

https://doi.org/10.1007/7726

Keywords:

2, 3-benzodiazepine, thione, alkylation, cyclization, NMR analysis, synthesis.

Abstract

1-Aryl-2-[(1-aryl-5H-2,3-benzodiazepin-4-yl)sulfanyl]ethanones were obtained by the alkylation of 1-aryl-2,3-benzodiazepine-4(3H,5H)thiones with 1-aryl-2-bromoethanones. A reaction for the annulation of the thiophene core to the 1,2-diazepine ring as a result of intramolecular cyclization involving a 4-aroylmethylsulfanyl substituent and C(4)–C(5) bond of diazepine was developed. Derivatives of a new thieno[2,3-d][2,3]benzodiazepine heterocyclic system were synthesized.

Author Biographies

Natalia M. Bohdan, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine

Senior Researcher of lab of the condensed heterocyclic compounds

Diana S. Stepanova, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine

Junior Researcher of lab of the condensed heterocyclic compounds

Serhii Yu. Suikov, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine

Senior Researcher of DEPARTMENT OF PHYSICOCHEMICAL INVESTIGATIONS

Vadim Yu. Popov, L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 50 Kharkivs'ke Road, Kyiv 02155, Ukraine

Junior Researcher of Heterocyclic Chemistry department

Yuri V. Ishkov, I. I. Mechnikov Odesa National University, 2 Dvoryanskaya St., Odesa 65082, Ukraine

Prfessor and Chair of Organc and Bioorganic Chemstry department

Serhii L. Bohza, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 50 Kharkivs'ke Road, Kyiv 02155, Ukraine

Head of lab of the condensed heterocyclic compounds,  Institute of organic chemistry NAS of Ukraine

Professor of Organic Chemistry dept. at Donetsk National University in Vinnitsa, Ukraine

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers