1,3‐Dipolar cycloaddition reactions of nitrile oxides and nitrile imines with 2‐methoxyvinyl phenyl ketone | Zendy

CoutouliArgyropoulou E. | Zendy; Thessalonikeos E. | Zendy

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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.

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