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 | |
| Publication status | Published - 1 Sep 1990 |
| Externally published | Yes |
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Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides. / Vasilevskii, S. F.; Shvartsberg, M. S.
In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 39, No. 9, 01.09.1990, p. 1901-1905.Research output: Contribution to journal › Article
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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.
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
VL - 39
SP - 1901
EP - 1905
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 0568-5230
IS - 9
ER -