Regioselective synthesis of thiophene fused sultam derivatives via iodocyclization approach and their application towards triazole linker

Deepak Kumar Barange, Veerababurao Kavala, Chun Wei Kuo, Cheng Chuan Wang, R. R. Rajawinslin, Janreddy Donala, Ching-Fa Yao

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

An efficient regioselective synthesis of 4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide derivatives via iodocyclization approach using iodine under mild reaction condition described herein. This coupling-iodocyclization strategy tolerated a variety of functional groups such as alkyl, cycloalkyl, phenyl producing the six-membered heterocyclic ring selectively. The resulting 4-iodo-2,3-disubstituted-2H-thieno[3,2-e][1,2]thiazine-1,1-dioxide was coupled with a variety of boronic acids (Suzuki coupling) and activated alkenes (Heck coupling). The iodo group was utilized for Sonogashira coupling followed by efficient transformation to azido precursor, which was used for the synthesis of various thieno-sultam linked with triazole.

Original languageEnglish
Pages (from-to)7598-7605
Number of pages8
JournalTetrahedron
Volume70
Issue number41
DOIs
Publication statusPublished - 2014 Oct 14

Fingerprint

Thiazines
Thiophenes
Triazoles
Boronic Acids
Derivatives
Alkenes
Iodine
Functional groups
naphthosultone

Keywords

  • Fused sultam
  • Iodocyclization
  • Regioselective synthesis
  • Sonogashira, Heck and Suzuki coupling
  • Triazole linker

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Regioselective synthesis of thiophene fused sultam derivatives via iodocyclization approach and their application towards triazole linker. / Barange, Deepak Kumar; Kavala, Veerababurao; Kuo, Chun Wei; Wang, Cheng Chuan; Rajawinslin, R. R.; Donala, Janreddy; Yao, Ching-Fa.

In: Tetrahedron, Vol. 70, No. 41, 14.10.2014, p. 7598-7605.

Research output: Contribution to journalArticle

Barange, Deepak Kumar ; Kavala, Veerababurao ; Kuo, Chun Wei ; Wang, Cheng Chuan ; Rajawinslin, R. R. ; Donala, Janreddy ; Yao, Ching-Fa. / Regioselective synthesis of thiophene fused sultam derivatives via iodocyclization approach and their application towards triazole linker. In: Tetrahedron. 2014 ; Vol. 70, No. 41. pp. 7598-7605.
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AU - Wang, Cheng Chuan

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