Synthesis of novel pyrazolo[5,1-b] [1,3]benzothiazoles: A new pericyclic pathway

Betül Tekiner-Gulbas, László Filák, Gyöngyvér Ágnes Vaskó, Orsolya Egyed, Ismail Yalçin, Esin Aki-Sener, Zsuzsanna Riedl, György Hajós

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

2-Benzylbenzothiazoles were easily N-aminated by tosyl hydroxylamine, and the obtained N-amino salts were reacted with ethyl orthoformate to give new derivatives of the pyrazolo[5,1-b][1,3]benzothiazole ring system. Mechanistic considerations suggest that the ring closure reaction proceeds via deprotonation of the N-amino salt followed by electrocyclization to provide the tricyclic ring system. The procedure opens an easy access to variously substituted derivatives of the target ring system.

Original languageEnglish
Pages (from-to)2005-2012
Number of pages8
JournalHeterocycles
Volume75
Issue number8
DOIs
Publication statusPublished - Aug 1 2008

Keywords

  • Benzothiazole
  • Electrocyclization
  • Fused Pyrazole
  • N-Amination
  • Reaction Mechanism

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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