Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

Research output: Contribution to journal › Article

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

Fingerprint

ASJC Scopus subject areas

Chemistry(all)

Cite this

Vasilevskii, S. F., & Shvartsberg, M. S. (1990). Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 39(9), 1901-1905. https://doi.org/10.1007/BF00958258

@article{b684d6352bcd416687caaf1d72e73903,

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 = "9",

day = "1",

doi = "10.1007/BF00958258",

language = "English",

volume = "39",

pages = "1901--1905",

journal = "Russian Chemical Bulletin",

issn = "0568-5230",

publisher = "Consultants Bureau",

number = "9",

}

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.

UR - http://www.scopus.com/inward/record.url?scp=0012616610&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0012616610&partnerID=8YFLogxK

U2 - 10.1007/BF00958258

DO - 10.1007/BF00958258

M3 - Article

AN - SCOPUS:0012616610

VL - 39

SP - 1901

EP - 1905

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 0568-5230

IS - 9

ER -

Access to Document

10.1007/BF00958258