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Mannich reactions of carbonyl compounds and enamines with benzotriazole as the NH component
Author(s) -
Katritzky Alan R.,
Galuszka Barbara,
Rachwal Stanislaw,
Black Michael
Publication year - 1994
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.5570310438
Subject(s) - chemistry , benzotriazole , mannich reaction , methylene , reactivity (psychology) , mannich base , organic chemistry , boron trifluoride , hydroxymethyl , formaldehyde , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
Boron trifluoride catalyses reactions of 1‐(hydroxymethyl)benzotriazole with ketones to give predominantly monosubstituted Mannich products. In unsymmetrical ketones, a methylene is slightly more reactive than a methyl group. For 1,3‐diketones and diethyl malonate, substitution occurs on the central methylene group. β‐Aminocrotononitrile and β‐aminocrotonate undergo Mannich condensations with benzotri‐azole and formaldehyde without any catalyst. Preliminary investigations of the reactivity of the Mannich bases thus obtained are reported.