Synthesis and structure determination of alicycle-fused thiazolo- and thiazino[2,3-bquinazolones and cycloalkylimino-3(N)-thiazolinylthiazolidines

Imre Huber, Ágnes Szabó, Ferenc Fülöp, Gábor Bernáth, Pál Sohár

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Starting from various stereoisomeric, alicyclic ethyl 2-aminocarboxylates (1-6, 23, 24) and 2-chloroethyl, 3-chloropropyl or 3-bromopropyl isothiocyanate, ring-closure reactions were performed under mild conditions. Thus, partially saturated thiazolo- and thiazino[2,3-b]quinazolinone derivatives (7-8) and asymmetric 2-[2′-(ethoxycarbonyl-cycloalkyl and -cycloalkenyl)-imino]-3-(2″-thiazolin-2″-yl)-thiazolidine diadducts (19-22) were formed. The structures of the new compounds were proved via their IR, 1H and 13C NMR spectra, use also being made of DR, DNOE, DEPT and 2D-HSC measurements.

Original languageEnglish
Pages (from-to)4949-4956
Number of pages8
JournalTetrahedron
Volume48
Issue number23
DOIs
Publication statusPublished - Jun 5 1992

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Keywords

  • alicyclic ethyl 2-aminocarboxylates
  • cycloalkylimino-3(N)-thiazolinylthiazolidines
  • haloalkyl isothiocyanates
  • thiazolo- and thiazino[2,3-b]quinazolones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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