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Lewis‐acid promoted aromatic cyclization of α‐chlorosulfides: Synthesis of ethyl isothiochroman‐1‐carboxylate and related compounds
Author(s) -
Ishibashi Hiroyuki,
Okada Motofumi,
Iida Kyoko,
Ikeda Masazumi
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220611
Subject(s) - chemistry , methylene , chloride , carboxylate , carboxylic acid , organic chemistry , lewis acids and bases , ethyl ester , medicinal chemistry , catalysis
A variety of ethyl isothiochroman‐1‐carboxylates and related compounds were synthesized by treatment of 2‐chloro‐2‐[(2‐arenyl)ethylthio]acetates with stannic chloride in methylene chloride. The same procedure was applied to the synthesis of ethyl 4‐chloro‐4‐methyltetrahydrothiopyran‐2‐carboxylate. Some isothiochroman‐1‐carboxylic acids were prepared and evaluated for antiinflammatory activity. Among the compounds tested, 7‐phenoxyisothiochroman‐1‐carboxylic acid showed weak activity.