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1,3‐Dipolar cycloaddition reactions of nitrile oxides and nitrile imines with 2‐methoxyvinyl phenyl ketone
Author(s) -
CoutouliArgyropoulou E.,
Thessalonikeos E.
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.5570280242
Subject(s) - nitrile , chemistry , regioselectivity , ketone , cycloaddition , methanol , 1,3 dipolar cycloaddition , medicinal chemistry , oxide , organic chemistry , catalysis
Nitrile oxides react regioselectively with 2‐methoxyvinyl phenyl ketone 1 to give 4‐benzoylisoxazoles 4 via elimination of methanol from the primary cycloadducts 3 . After heating with an excess of nitrile oxide bis‐cycloadducts 5 were also formed. Reactions of nitrile imines with 1 are less regioselective yielding both 4‐benzoylpyrazoles 9 and 5‐benzoytpyrazoles 10 , whereas no bis‐cycloadducts were isolated.