Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

Abstract

Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or fivemembered lactam ring. The formation of a γ-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

Original language	English
Pages (from-to)	1901-1905
Number of pages	5
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	39
Issue number	9
DOIs	https://doi.org/10.1007/BF00958258
Publication status	Published - 1 Sep 1990
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1007/BF00958258

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title = "Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides",

abstract = "Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or fivemembered lactam ring. The formation of a γ-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.",

author = "Vasilevskii, {S. F.} and Shvartsberg, {M. S.}",

year = "1990",

month = sep,

day = "1",

doi = "10.1007/BF00958258",

language = "English",

volume = "39",

pages = "1901--1905",

journal = "Russian Chemical Bulletin",

issn = "0568-5230",

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TY - JOUR

T1 - Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

AU - Vasilevskii, S. F.

AU - Shvartsberg, M. S.

PY - 1990/9/1

Y1 - 1990/9/1

N2 - Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or fivemembered lactam ring. The formation of a γ-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

AB - Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or fivemembered lactam ring. The formation of a γ-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

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