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Furan ring opening — isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes

✍ Scribed by Vladimir T. Abaev; Artem S. Dmitriev; Sergey A. Podelyakin; Alexander V. Butin; Andrey V. Gutnov

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
498 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2furyl)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 = tertbutyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions.

📜 SIMILAR VOLUMES

Furan Ring Opening — Indole Ring Closure
Furan Ring Opening — Indole Ring Closure: Synthesis of Furo[2′,3′:3,4]cyclohepta[1,2-b]indolium Chlorides.
✍ Alexander V. Butin; Sergey K. Smirnov; Tatyana A. Stroganova 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 23 KB 👁 1 views

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Furan ring opening - indole ring closure
Furan ring opening - indole ring closure: Synthesis of furo[2′,3′:3,4]-cyclohepta[1,2-b]indolium chlorides
✍ Alexander V. Butin; Sergey K. Smirnov; Tatyana A. Stroganova 📂 Article 📅 2006 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 365 KB

## Abstract magnified image A new synthetic approach to furo[2′,3′:3,4]cyclohepta[1,2‐__b__]indolium chlorides is elaborated starting from 2‐acetylaminoaryldifurylmethanes or 2‐aminoaryldifurylmethanes under treatment with methanolic HCl solution. The reaction proceeds in three steps: recyclizatio