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Synthesis 2006(9): 1433-1436  
DOI: 10.1055/s-2006-926438
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sulfones in the Pyrrolo[2,1-b]thiazole Series

Anton V. Tverdokhlebov*a, Alexander P. Andrushkoa, Andrey A. Tolmachevb
a Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
b Kiev National Taras Shevchenko University, Volodimirska str. 62, 01033 Kiev, Ukraine
Fax: +380(44)5586553; e-Mail: atver@univ.kiev.ua;
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Publikationsverlauf

Received 7 November 2005
Publikationsdatum:
11. April 2006 (online)

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Abstract

(Arylsulfonyl)acetonitriles were shown to react with mercaptoacetic acid in refluxing pyridine yielding 2-[(arylsulfonyl)methylidene]thiazolidin-4-ones. The latter underwent alkylation with α-bromoketones in the presence of K2CO3 selectively at the nitrogen atom. Further formylation of the resulting phenacyl derivatives with excess DMF·POCl3 complex afforded 5-aroyl-7-arylsulfonyl-2-[(dimethylamino)methylidene]pyrrolo[2,1-b]thiazol-3(2H)-ones.

Key words

alkylations - nitriles - pyrrolo[2,1-b]thiazoles - sulfones - Vilsmeier complex

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