Synthesis of substituted propargylamines from aminals and phenylacetylen in the presence of Cu(I) halides
Aminals, the condensation products of carbonyl compounds with secondary amines (1), have been examined within a general scheme for the Mannich reaction (2), as precursors of iminium ions. The authors investigated the behavior of aminals derived from aromatic aldehydes upon heating with phenylacetylene and CuX (X = I, Br, Cl) in acetonitrile. The authors assumed that an aminal, acting as an HX acceptor, would lead to the formation of copper phenylacetylide, and be itself converted via this process to an iminium salt, which could then participate in an aminomethylation reaction of copper phenylacetylide. It was found that propargylamines were formed rapidly upon heating stoichiometric amounts of the reagents in acetonitrile solution.
- Research Organization:
- M. A. Suslov Rostov State Univ. (USSR)
- OSTI ID:
- 7160038
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:6; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACETONITRILE
ALDEHYDES
ALKYNES
AMINES
BROMIDES
BROMINE COMPOUNDS
CATALYSIS
CATALYTIC EFFECTS
CHLORIDES
CHLORINE COMPOUNDS
COPPER BROMIDES
COPPER CHLORIDES
COPPER COMPOUNDS
COPPER HALIDES
COPPER IODIDES
HALIDES
HALOGEN COMPOUNDS
HETEROGENEOUS CATALYSIS
HYDROCARBONS
IODIDES
IODINE COMPOUNDS
NITRILES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SYNTHESIS
TEMPERATURE DEPENDENCE
TRANSITION ELEMENT COMPOUNDS