Unexpected results in the heterocyclization of 5-acetylenylpyrazole-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)

Sergei F. Vasilevsky, Elena V. Mshvidobadze, Victor I. Mamatyuk, Galina V. Romanenko, Jose Elguero

Research output: Contribution to journal › Article

16 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4457-4459
Number of pages3
JournalTetrahedron Letters
Volume46
Issue number26
DOIs
Publication statusPublished - 27 Jun 2005
Externally publishedYes

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X ray crystallography
X Ray Crystallography
Cyclization
Carboxylic Acids

Keywords

  • Cross-coupling
  • Hetarylacetylenes
  • Heterocyclization
  • Pyrazolopyridines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Unexpected results in the heterocyclization of 5-acetylenylpyrazole-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). / Vasilevsky, Sergei F.; Mshvidobadze, Elena V.; Mamatyuk, Victor I.; Romanenko, Galina V.; Elguero, Jose.

In: Tetrahedron Letters, Vol. 46, No. 26, 27.06.2005, p. 4457-4459.

Research output: Contribution to journal › Article

Vasilevsky, SF, Mshvidobadze, EV, Mamatyuk, VI, Romanenko, GV & Elguero, J 2005, 'Unexpected results in the heterocyclization of 5-acetylenylpyrazole-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, vol. 46, no. 26, pp. 4457-4459. https://doi.org/10.1016/j.tetlet.2005.04.127
Vasilevsky SF, Mshvidobadze EV, Mamatyuk VI, Romanenko GV, Elguero J. Unexpected results in the heterocyclization of 5-acetylenylpyrazole-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 Jun 27;46(26):4457-4459. https://doi.org/10.1016/j.tetlet.2005.04.127
Vasilevsky, Sergei F. ; Mshvidobadze, Elena V. ; Mamatyuk, Victor I. ; Romanenko, Galina V. ; Elguero, Jose. / Unexpected results in the heterocyclization of 5-acetylenylpyrazole-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). In: Tetrahedron Letters. 2005 ; Vol. 46, No. 26. pp. 4457-4459.
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