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Ambident reactivity of a thiazolo[3,2‐ a ]pyridinium salt with nucleophiles
Author(s) -
Hajós Gy,
Messmer A.
Publication year - 1984
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.5570210334
Subject(s) - pyridinium , chemistry , reactivity (psychology) , nucleophile , salt (chemistry) , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Reaction of thiazolo[3,2‐ a ]pyridinium salt 1 with secondary amines, depending on the reaction condition, may result in both stable pseudo bases 2 as addition products and thiazolyl‐dieneamines 4 as products of ring opening. The ambident reactivity of the title system is interpreted by frontier orbital theory.