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Title: 2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols
Authors: Obydennov, D. L.
Simbirtseva, A. E.
Piksin, S. E.
Sosnovskikh, V. Y.
Issue Date: 2020
Publisher: American Chemical Society
Citation: 2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols / D. L. Obydennov, A. E. Simbirtseva, S. E. Piksin, et al. — DOI 10.1021/acsomega.0c05357 // ACS Omega. — 2020. — Vol. 5. — Iss. 51. — P. 33406-33420.
Abstract: In this work, a three-stage and easily scalable synthesis of 2,6-dicyano-4-pyrone (overall yield of 45%) as a new convenient building block has been developed from diethyl acetonedioxalate. It was shown that the transformation with hydroxylamine and [3 + 2]-cycloaddition, in contrast to the reactions with hydrazines, selectively proceed through the attack at the cyano groups without the pyrone ring-opening to give symmetrical and unsymmetrical pyrone-bearing heterocyclic triads containing 1,2,4- and 1,3,4-oxadiazoles as well as tetrazole moieties. The reaction of 2,6-bis(hetaryl)-4-pyrones with ammonia afforded 2,6-bis(hetaryl)pyridines in 63-87% yields. The 4-pyridone/4-pyridinol tautomerism of 2,6-bis(hetaryl)pyridinols and the influence of the nature of adjacent azolyl moieties on this equilibrium have been discussed. © 2020 The Authors. Published by American Chemical Society.
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85098973418
PURE ID: 20895562
ISSN: 24701343
DOI: 10.1021/acsomega.0c05357
metadata.dc.description.sponsorship: This work was financially supported by the Russian Science Foundation (grant 18-13-00186). Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch) and the Laboratory of Complex Investigations and Expert Evaluation of Organic Materials of the Center for Joint Use at the Ural Federal University (UrFU). The authors would like to thank Suslova A.I. and Morozova A.P. for their help in this work.
RSCF project card: 18-13-00186
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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