Sequential Amination/Annulation/Aromatization Reaction of Carbonyl Compounds and Propargylamine:  A New One-Pot Approach to Functionalized Pyridines

A general one-pot synthesis of pyridines 4a−t from the reaction of dialkyl acyclic/cyclic ketones 1a−i, methyl, aryl/heteroaryl ketones 1m−r, and aldehydes bearing α-hydrogens 1s,t with propargylamine 2 is described. Gold and copper salts are efficient catalysts for the reaction of ketones with 2. T...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-09, Vol.68 (18), p.6959-6966
Main Authors: Abbiati, Giorgio, Arcadi, Antonio, Bianchi, Gabriele, Di Giuseppe, Sabrina, Marinelli, Fabio, Rossi, Elisabetta
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:A general one-pot synthesis of pyridines 4a−t from the reaction of dialkyl acyclic/cyclic ketones 1a−i, methyl, aryl/heteroaryl ketones 1m−r, and aldehydes bearing α-hydrogens 1s,t with propargylamine 2 is described. Gold and copper salts are efficient catalysts for the reaction of ketones with 2. The formation of the pyridines 4 is suggested to proceed through the sequential amination of carbonyl compounds followed by regioselective 6-endo-dig cyclization of the N-propargylenamine (N-propargyldienamine) intermediate 3(5) and aromatization reaction. Whereas the preparation of linear polycyclic pyridine 4i can be carried out by reacting cholestan-3-one 1i with 2, the angular polycyclic pyridine 4j has been obtained starting from cholest-5-en-3-one 1j. Selectivity of the reaction of polycyclic dicarbonyls 1k,l with 2 has also been investigated.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0347260