Selective Ring Openings of Isomeric Fused Thiazolium Salts with Nucleophiles

G. Hajos, A. Messmer, T. Koritsanszky

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Abstract

Different types of reactions have been found with isomeric tricyclic fused thiazolium salts for their interactions with secondary amines. Thus, the angularly fused quinolinium salt 7 gave rise to a stable pseudobase 8; the related angular isoquinolinium system 9 led to opening of the thiazole ring and enamine 10 was formed; and the linear system 6 underwent opening of the pyridine moiety and gave the aldehyde compound 16. The reactions were interpreted on FMO theory; the CNDO/2 calculation supported the qualitative picture based on the “annelation effect”.

Original languageEnglish
Pages (from-to)2015-2018
Number of pages4
JournalJournal of Organic Chemistry
Volume52
Issue number10
DOIs
Publication statusPublished - May 1 1987

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ASJC Scopus subject areas

  • Organic Chemistry

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