Synthesis 2017; 49(10): 2223-2230
DOI: 10.1055/s-0036-1588407
paper
© Georg Thieme Verlag Stuttgart · New York

Formal [3+3] Cyclocondensation of 4-Acyl-1H-pyrrole-2,3-diones with Five-Membered Cyclic Enamines To Form Substituted 1H-Py­razolo[3,4-b]pyridines and Isoxazolo[5,4-b]pyridines

Alexey Yu. Dubovtsev
Department of Chemistry, Perm State University, Bukireva St. 15, Perm 614990, Russian Federation   eMail: koh2@psu.ru
,
Maksim V. Dmitriev
Department of Chemistry, Perm State University, Bukireva St. 15, Perm 614990, Russian Federation   eMail: koh2@psu.ru
,
Pavel S. Silaichev
Department of Chemistry, Perm State University, Bukireva St. 15, Perm 614990, Russian Federation   eMail: koh2@psu.ru
,
Dmitriy I. Antonov
Department of Chemistry, Perm State University, Bukireva St. 15, Perm 614990, Russian Federation   eMail: koh2@psu.ru
,
Аndrey N. Maslivets*
Department of Chemistry, Perm State University, Bukireva St. 15, Perm 614990, Russian Federation   eMail: koh2@psu.ru
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Publikationsverlauf

Received: 19. Oktober 2016

Accepted after revision: 10. Januar 2017

Publikationsdatum:
31. Januar 2017 (online)


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Abstract

A highly efficient method for the preparation of multifunctional substituted 1H-pyrazolo[3,4-b]pyridines and isoxazolo[5,4-b]pyridines was developed through the formal [3+3] cascade cyclocondensation of 4-acyl-1H-pyrrole-2,3-diones as 1,3-bis-electrophiles with the five-membered cyclic enamines as 1,3-bis-nucleophiles.

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