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Synthesis 2012(8): 1263-1267  
DOI: 10.1055/s-0031-1290808
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Easy Synthesis of Novel 4-Azolylpyridazin-3-ones

Oleksandr V. Geraschenko*a,b, Pavel V. Khodakovskiya, Oleksandr N. Shivanyukb, Oleg V. Shishkinc, Pavel K. Mykhailiuk*a,b, Andrey A. Tolmacheva,b
a Enamine Ltd., Aleksandra Matrosova Street 23, Kyiv 01103, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine
Fax: +380(44)2351273; e-Mail: Geraschenko.Aleksandr@gmail.com; e-Mail: Pavel.Mykhailiuk@gmail.com;
c STC, Institute for Single Crystals, National Academy of Science of Ukraine, Lenina Avenue 60, Kharkiv 61001, Ukraine
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Publikationsverlauf

Received 1 December 2011
Publikationsdatum:
27. März 2012 (online)

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Abstract

Ethyl azol-2-ylglyoxylates react smoothly with acetone in the presence of catalytic amounts of proline and trifluoroacetic acid to give the corresponding azolyl aldols in 93-98% yield. The products are easily transformed into azolyl pyridazinones in 85-98% yield by cyclization with hydrazine hydrate.

Key words

heterocycles - cyclizations - pyridazines - ketones - esters - catalysis

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