Synthesis 2013; 45(7): 925-930
DOI: 10.1055/s-0032-1318329
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Pyrazolo[1,5-a]pyrimidines by Reaction of β,γ-Unsaturated γ-Alkoxy-α-keto Esters with N-Unsubstituted 5-Aminopyrazoles

Oleksandr O. Stepaniuk
a   Kyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine
b   Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
,
Vitalii O. Matviienko
a   Kyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine
b   Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
,
Ivan S. Kondratov*
b   Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
c   Institute of Bioorganic Chemistry and Petrochemistry, National Ukrainian Academy of Science, Murmanska 1, 02660 Kyiv-94, Ukraine   Fax: +380(44)537325   Email: vanya_ko@mail.ru
,
Igor V. Vitruk
a   Kyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine
b   Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
,
Andrei O. Tolmachev
a   Kyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kyiv-33, Ukraine
b   Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
› Author Affiliations
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Publication History

Received: 05 December 2012

Accepted after revision: 08 February 2013

Publication Date:
04 March 2013 (online)


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Abstract

The reaction of β,γ-unsaturated γ-alkoxy-α-keto esters with N-unsubstituted 5-aminopyrazoles was investigated. The reaction proceeds with high regioselectivity and is considered as an effective­ method for the preparation of new pyrazolo[1,5-a]pyrimidines bearing an ester function in the 7-position. The obtained drug-like compounds have a great potential for medicinal chemistry as they closely resemble the structure of several marketed pharmaceuticals.

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