Study on selectivity in the reaction of 2-substituted pyridinium-N-imines with dimethyl acetylenedicarboxylate

Study on selectivity in the reaction of 2-substituted pyridinium-N-imines with dimethyl acetylenedicarboxylate Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2016, Volume: 57, Number: 10, Pages: 1093-1096 Pages count : DOI: 10.1016/j.tetlet.2016.01.092

Tags

1,3-Dipolar cycloaddition; N-Amine salts; Pyrazolo[1,5-alpha]pyridines; Selectivity; C-X bond cleavage; DFT calculations

Authors

Supranovich Vyacheslav I. ^1,2 , Vorob'ev Aleksey Yu. ^1,2 , Borodkin Gennady I. ^1,2 , Gatilov Yury V. ^1,2 , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Acad Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogov St 2, Novosibirsk 630090, Russia

Reactions of 2-X-pyridinium-N-imines (X = F, Cl, Br, CN, OPh, NH2, N-morpholine) with dimethyl acetylenedicarboxylate (DMAD) have been studied. In the case of X = Cl, Br, CN, OPh both 7-substituted and 7-H-pyrazolo[1,5-alpha]pyridines are formed. The 7-H/7-X ratio usually increases with the growing solvent polarity. The reaction of N-amino-2-iminopyridine with DMAD gives substituted pyrido[1,2-b] [1,2,4]triazine. (C) 2016 Elsevier Ltd. All rights reserved.

Supranovich V.I. , Vorob'ev A.Y. , Borodkin G.I. , Gatilov Y.V. , Shubin V.G.
Study on selectivity in the reaction of 2-substituted pyridinium-N-imines with dimethyl acetylenedicarboxylate
Tetrahedron Letters. 2016. V.57. N10. P.1093-1096. DOI: 10.1016/j.tetlet.2016.01.092 WOS РИНЦ

Published print:

Mar 1, 2016

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