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Synthesis 2011(2): 251-256  
DOI: 10.1055/s-0030-1258371
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 6-Amino-2-bromo-4-hydroxynicotinaldehyde Derivatives

Alexander V. Denisenkoa, Anton V. Tverdokhlebov*b, Andrey A. Tolmacheva,b, Yulian M. Volovenkoa, Svitlana V. Shishkinac, Oleg V. Shishkinc
a Kiev National Taras Shevchenko University, Volodimirska str., 62, 01033 Kiev, Ukraine
b Enamine Ltd., Alexandra Matrosova str., 23, 01103 Kiev, Ukraine
Fax: +380445373253; e-Mail: atver@univ.kiev.ua;
c STC Institute for Single Crystals, NAS of Ukraine, 60 Lenina ave., 61001 Kharkiv, Ukraine
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Publikationsverlauf

Received 26 October 2010
Publikationsdatum:
20. Dezember 2010 (online)

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Abstract

Acylation of (1,3-dimethylbenzimidazol-2-ylidene)-, (3-methylbenzothiazol-2-ylidene)-, and (3,4-dimethylthiazol-2-ylidene)-acetonitriles with 1-(cyanoacetyl)-3,5-dimethylpyrazole was found to proceed at the exocyclic carbon atom, yielding the appropriate 2-heterylidene-3-oxopentanedinitriles. Treatment of the prepared dinitriles with hydrobromic acid in refluxing acetic acid afforded 2-(6-amino-2-bromo-4-hydroxypyridin-3-yl)-substituted quaternary salts of benzimidazolium, benzothiazolium, and thiazolium. Their structures were confirmed unambiguously by X-ray crystallographic studies. Reduction of these quaternary salts with excess sodium borohydride yielded the corresponding dihydro (in the case of benzoazoles) or tetrahydro (in the case of thiazole) derivatives, which were shown to be synthetic equivalents of the title nicotinaldehyde.

Key words

aldehydes - heterocycles - hydrazones - nitriles - pyridines

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