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Photocycloadditions on 2‐Methyloxazolo[5,4‐ b ]pyridine
Author(s) -
Donati Donato,
Fusi Stefania,
Ponticelli Fabio
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:24<4211::aid-ejoc4211>3.0.co;2-u
Subject(s) - methacrylonitrile , chemistry , furan , ether , yield (engineering) , pyridine , organic chemistry , vinyl ether , medicinal chemistry , copolymer , materials science , acrylonitrile , metallurgy , polymer
The title compound undergoes photocycloadditions with both electron‐poor alkenes (methacrylonitrile) and electron‐rich alkenes (ethyl vinyl ether and furan). The initial photoadducts evolve into a variety of compounds. In the photoreaction with methacrylonitrile, oxazoloazocines 5 and 7 and cyclopentenylidenes 6 Z and 6 E are obtained; the photoadducts with vinyl ether yield oxazoloazocines 9 and 11 , substituted oxazoles 10 and 12 , and pyrrolopyridine 13 ; from the reaction with furan the furylpyridine 14 was isolated. (© Wiley‐VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2002)