Unexpected cleavage of the C-py-C-py bond in the reaction of 2,2 '-bipyridine N,N '-diimines with acetylenes

Unexpected cleavage of the C-py-C-py bond in the reaction of 2,2 '-bipyridine N,N '-diimines with acetylenes Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2014, Volume: 55, Number: 39, Pages: 5377-5380 Pages count : DOI: 10.1016/j.tetlet.2014.08.015

Tags

1,3-Dipolar cycloaddition; N-Amine salts; Pyrazolo[1,5-a]pyridines; DFT calculations; C-sp2-C-sp2 bond cleavage

Authors

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

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk, Russia

An unusual cleavage of the C-py-C-py bond in the reaction of 2,2'-bipyridine N,N'-diimine and its C-methyl substituted derivatives with acetylenes is described. The effect of the solvent on the yield of 7,7'-bipyrazolo[1,5-a]pyridine-2,2',3,3'-tetracarboxylates and the products of cleavage of the C-py-C-py bond has been studied. The mechanism of the cleavage reaction is discussed on the basis of DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.

Supranovich V.I. , Borodkin G.I. , Vorob'ev A.Y. , Shubin V.G.
Unexpected cleavage of the C-py-C-py bond in the reaction of 2,2 '-bipyridine N,N '-diimines with acetylenes
Tetrahedron Letters. 2014. V.55. N39. P.5377-5380. DOI: 10.1016/j.tetlet.2014.08.015 WOS Scopus РИНЦ

Published print:

Sep 1, 2014

Web of science	WOS:000341901100008
Scopus	2-s2.0-84906961189
Elibrary	23987832
OpenAlex	W2950871582