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Synthesis 2003(17): 2632-2638  
DOI: 10.1055/s-2003-42451
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Approach to Pyrrolo[2,1-b]thiazoles

Anton V. Tverdokhlebov*a, Elizaveta V. Resnyanskaa, Andrey A. Tolmachevb, Alexander P. Andrushkoa
a Enamine Ltd. Co., I. Kudry str. 31, apt.17, 02042, Kiev, Ukraine
b Kiev National Taras Shevchenko University, Volodimirska str., 62, 01033, Kiev, Ukraine
e-Mail: atver@mail.univ.kiev.ua;
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Publikationsverlauf

Received 19 May 2003
Publikationsdatum:
23. Oktober 2003 (online)

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Abstract

5-Aroyl-2-(dimethylamino)methylidene-2,3-dihydro-3-oxopyrrolo[2,1-b]thiazole-7-carboxylic acid esters, -7-carbonitriles and corresponding 7-hetaryl substituted derivatives were prepared. Thus, the substituted acetonitriles (XCH2CN, where X = CO2R, CN, hetaryl) were treated with mercaptoacetic acid yielding 2-(X-methylidene)thiazolidin-4-ones, which were N-alkylated with phenacyl bromides. Further formylation of the obtained compounds with excess of DMF·POCl3 complex led to the above mentioned pyrrolo[2,1-b]thiazoles.

Key words

alkylations - heterocycles - pyrrolo[2,1-b]thiazoles - ring closure - 4-thiazolidinones

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