Unexpected results in the heterocyclization of 5-acetylenyl-pyrazole-4-carboxylic acid hydrazides under the influence of CuCl: formation of a diazepinone and dehydrodimerization into the corresponding bis(pyrazolo[4,3-d][1,2]diazepinone)

Unexpected results in the heterocyclization of 5-acetylenyl-pyrazole-4-carboxylic acid hydrazides under the influence of CuCl: formation of a diazepinone and dehydrodimerization into the corresponding bis(pyrazolo[4,3-d][1,2]diazepinone) Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2005, Volume: 46, Number: 26, Pages: 4457-4459 Pages count : 3 DOI: 10.1016/j.tetlet.2005.04.127

Tags

pyrazolopyridines; cross-coupling; hetarylacetylenes; heterocyclization

Authors

Vasilevsky Sergei F. ¹ , Mshvidobadze Elena V. ¹ , Mamatyuk Victor I. ² , Romanenko Galina V. ³ , Elguero Jose ⁴

Affiliations

1	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Int Tomog Ctr, Siberian Branch, Novosibirsk 630090, Russia
4	(Данные Web of science) CSIC, Inst Quim Med, E-28006 Madrid, Spain

The simple reaction of cyclization of hydrazides of vic-acetylenylbenzoic and acetylenylpyrazole carboxylic acid can lead to four different compounds: five-membered N-aminolactams, six-membered N-aminolactams, six-membered diazinones and diazepinones, but only the first three have been described. In this paper we report the unexpected formation of a bis(pyrazolo[4,3-d][1,2]diazepinone, the structure of which has been established by X-ray crystallography. (c) 2005 Elsevier Ltd. All rights reserved.

Vasilevsky S.F. , Mshvidobadze E.V. , Mamatyuk V.I. , Romanenko G.V. , Elguero J.
Unexpected results in the heterocyclization of 5-acetylenyl-pyrazole-4-carboxylic acid hydrazides under the influence of CuCl: formation of a diazepinone and dehydrodimerization into the corresponding bis(pyrazolo[4,3-d][1,2]diazepinone)
Tetrahedron Letters. 2005. V.46. N26. P.4457-4459. DOI: 10.1016/j.tetlet.2005.04.127 WOS Scopus РИНЦ

Published print:

Jun 1, 2005

Web of science	WOS:000229844600008
Scopus	2-s2.0-19544362859
Elibrary	13495054
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