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Photocyclization reactions. Part 1. Synthesis of dihydrobenzofuranols using photocyclization of 2‐alkoxybenzaldehydes, 2′‐alkoxyacetophenones, 2‐formylphenoxyacetic acids and 2‐acetylphenoxyacetic acids
Author(s) -
Horaguchi Takaaki,
Tsukada Chikara,
Hasegawa Eietsu,
Shimizu Takahachi,
Suzuki Tsuneo,
Tanemura Kiyoshi
Publication year - 1991
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.5570280518
Subject(s) - chemistry , decarboxylation , substituent , acetonitrile , irradiation , medicinal chemistry , organic chemistry , stereochemistry , catalysis , physics , nuclear physics
Photocyclization reactions were carried out on 2‐alkoxybenzaldehydes 1a‐f , 2′‐alkoxyacetophenones 2a‐h , 2‐formylphenoxyacetic acids 1i‐l and 2‐acetylphenoxyacetic acids 2i‐m . Irradiation of 1a‐f and 2a‐h in acetonitrile gave the corresponding dihydrobenzofuranols 3, 5 and dihydroisobenzofuranols 4, 6 . Using carboxylic acids 1i‐1, 2i‐m as starting materials, decarboxylation occurred immediately to give the corresponding ethers 1a‐d, 2a‐e . Further irradiation of the solution afforded dihydrobenzofuranols 3, 5 and dihydroisobenzofuranols 4, 6 . Substituent effects on photocyclization and reaction pathways are discussed.