SILVER CATALYZED CYCLIZATION OF ALKYNOIC ACIDS - EFFICIENT SYNTHESIS OF 3-ALKYLIDENEPHTHALIDES, GAMMA-ALKYLIDENEBUTENOLIDES, AND GAMMA-ALKYLIDENEBUTYROLACTONES

Authors
OGAWA Y MARUNO M WAKAMATSU T
Citation
Y. Ogawa et al., SILVER CATALYZED CYCLIZATION OF ALKYNOIC ACIDS - EFFICIENT SYNTHESIS OF 3-ALKYLIDENEPHTHALIDES, GAMMA-ALKYLIDENEBUTENOLIDES, AND GAMMA-ALKYLIDENEBUTYROLACTONES, Heterocycles, 41(11), 1995, pp. 2587-2599
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
41
Issue
11
Year of publication
1995
Pages
2587 - 2599
Database
ISI
SICI code
0385-5414(1995)41:11<2587:SCCOAA>2.0.ZU;2-2
Abstract
The cyclization of 2-pentynylbenzoic acid (1a) catalyzed by various si lver salts and solvents was investigated. 2-Alkynylbenzoic acids (1), 2-alken-4-ynoic acids (7), and 4-alkynoic acids (4) were effectively c yclized to the corresponding phthalides (2), gamma-alkylidenebutenolid es (8), and gamma-alkylidenebutyrolactones (5) with silver iodide or s ilver as catalyst in DMF regio- and stereo-selectively in excellent yi eld, respectively.