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

Imre Huber, Ágnes Szabó, F. Fülöp, G. Bernáth, P. 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

Fingerprint

Quinazolinones
Thiazolidines
Nuclear magnetic resonance
Derivatives
isothiocyanic acid
Carbon-13 Magnetic Resonance Spectroscopy
Proton Magnetic Resonance Spectroscopy

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Synthesis and structure determination of alicycle-fused thiazolo- and thiazino[2,3-bquinazolones and cycloalkylimino-3(N)-thiazolinylthiazolidines",
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.",
keywords = "alicyclic ethyl 2-aminocarboxylates, cycloalkylimino-3(N)-thiazolinylthiazolidines, haloalkyl isothiocyanates, thiazolo- and thiazino[2,3-b]quinazolones",
author = "Imre Huber and {\'A}gnes Szab{\'o} and F. F{\"u}l{\"o}p and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1992",
month = "6",
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doi = "10.1016/S0040-4020(01)81587-8",
language = "English",
volume = "48",
pages = "4949--4956",
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T1 - Synthesis and structure determination of alicycle-fused thiazolo- and thiazino[2,3-bquinazolones and cycloalkylimino-3(N)-thiazolinylthiazolidines

AU - Huber, Imre

AU - Szabó, Ágnes

AU - Fülöp, F.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1992/6/5

Y1 - 1992/6/5

N2 - 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.

AB - 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.

KW - alicyclic ethyl 2-aminocarboxylates

KW - cycloalkylimino-3(N)-thiazolinylthiazolidines

KW - haloalkyl isothiocyanates

KW - thiazolo- and thiazino[2,3-b]quinazolones

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M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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