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Inverse electron‐demand 1,3‐dipolar cycloaddition reactions of cyclooctyne with pyridinium bis(methoxycarbonyl)methylides
Author(s) -
Matsumoto Kiyoshi,
Hayashi Naoto,
Ikemi Yukio,
Toda Mitsuo,
Uchida Takane,
Aoyama Kinuyo,
Miyakoshi Yoshihiro
Publication year - 2001
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.5570380209
Subject(s) - pyridinium , chemistry , cycloaddition , 1,3 dipolar cycloaddition , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis
Cyclooctyne underwent 1,3‐dipolar cycloaddition with pyridinium bis(methoxy‐carbonyl)methylides to afford the corresponding indolizines (8‐methoxycarbonyl‐7‐azatricyclo[7.6.0.0 2‐7 ]pentadeca‐1,3,5,8‐tetraenes) in good to moderate yields. Some molecular orbital considerations are also described on this reaction compared with the results on the reaction of pyridinium dicyanomethylides with cyclooctyne.