Synthesis of 1,4-benzothiazin-2-yl derivatives of 1,3-dicarbonyl compounds and benzothiazinone spiro derivatives by the reaction of 2-chloro-1,4-benzothiazin-3-ones with 'push-pull' enamines

Konstantin G. Nazarenko, Nataliya A. Shtil, Sergey A. Buth, Alexander N. Chernega, Miron O. Lozinskii, Andrey A. Tolmachev

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The reaction of 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazines with 'push-pull' enamines was investigated. The reaction with the enamines occurs at the β-carbon atom in the presence of a small excess of triethylamine. As a result, a set of 3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-yl derivatives of 1,3-dicarbonyl compounds and benzothiazinone spiro derivatives was prepared. On acidic hydrolysis of ethyl 2-ethyl-3-(methylimino)-2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-yl)butanoate, a new rearrangement affording ethyl 11-ethyl-2,3-dimethyl-4-oxo-2,3,4,5-tetrahydro-1H-2,5-methano-6,1,3-benzothiadiazocine-11-carboxylate was discovered. A plausible mechanism and factors influencing the course of the reaction are discussed.

Original languageEnglish (US)
Pages (from-to)4478-4485
Number of pages8
JournalTetrahedron
Volume64
Issue number19
DOIs
StatePublished - May 5 2008

Keywords

  • Chloro derivatives
  • Electrophilic substitution
  • Enamines
  • Rearrangement
  • Spiro heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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