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Furan ring opening — isocoumarine ring closure: A recyclization reaction of 2‐carboxyaryldifurylmethanes
Author(s) -
Abaev Vladimir T.,
Dmitriev Artem S.,
Podelyakin Sergey A.,
Butin Alexander V.,
Gutnov Andrey V.
Publication year - 2006
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.5570430510
Subject(s) - chemistry , furan , ring (chemistry) , methanol , medicinal chemistry , chloride , hydrogen chloride , closure (psychology) , acetyl chloride , hydrogen , catalysis , organic chemistry , economics , market economy
A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5‐R‐2‐furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene‐1‐one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4‐(5‐R‐furan‐2‐yl)‐3‐(3‐oxo‐3‐R‐propyl)‐isochromene‐1‐ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert ‐butyl only corresponding 4‐[5‐( tert ‐butyl)‐2‐furyl]‐3‐(4,4‐dimethyl‐3‐oxopentyl)‐1‐isochromenones were isolated regardless of the reaction conditions.