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Synthesis 2007(12): 1811-1818  
DOI: 10.1055/s-2007-983713
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Masked 2-Amino-4,5-dihydro-4-oxopyrrole-3-carboxaldehydes

Anton V. Tverdokhlebov*a, Alexander V. Denisenkob, Andrey A. Tolmachevb, Yulian M. Volovenkob
a Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: atver@univ.kiev.ua;
b National Taras Shevchenko University of Kiev, Volodimirska str. 62, 01033 Kiev, Ukraine
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Publication History

Received 19 February 2007
Publication Date:
08 June 2007 (online)

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Abstract

2-(1-Substituted-2-amino-4,5-dihydro-4-oxopyrrol-3-yl)-1,3-dimethylbenzimidazolium and -3-methylbenzothiazolium chlorides were prepared by reaction of 2-(2,3-dihydro-1,3-dimethylbenzimidazol-2-ylidene)- and 2-(3-methylbenzothiazol-2-ylidene)-4-chloro-3-oxobutanenitriles with primary amines. The salts obtained were reduced to 4-(2,3-dihydro-1,3-dimethylbenzimidazol-2-yl)- and 4-(2,3-dihydro-3-methylbenzothiazol-2-yl)-1-substituted-5-aminopyrrol-3(2H)-ones. These pyrrole derivatives were shown to serve as synthetic equivalents of the corresponding 2-aminopyrrole-3-carboxaldehydes. Thus, their treatment with phenylhydrazine yielded 1-substituted 2-amino-4,5-dihydro-4-oxopyrrole-3-carboxaldehyde phenylhydrazones, whereas condensation with malonodinitrile afforded 1-substituted 6-amino-2,3-dihydro-3-oxopyrrolo[2,3-b]pyridine-5-carbonitriles.

Key words

amino aldehydes - heterocycles - nitriles - pyrroles - reductions­