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Cycloadditions of α‐Diazo Carbonyl Compounds to Enamines
Author(s) -
Huisgen Rolf,
Reissig HansUlrich
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197903301
Subject(s) - diazo , chemistry , ring (chemistry) , cycloaddition , enamine , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Carbonyl‐activated diazo compounds and enamines (acyclic or with a six‐membered ring) undergo 1,3‐dipolar cycloaddition. The invariant orientation of the reactants is remarkable: the initial products are 4‐aminopyrazolines such as (1) . In contrast, the (partly isolable) zwitterions (2) formed as primary products from enamines with a five‐membered ring arise by azo coupling.