One-step synthesis of thiazolo[3,2- a]pyridines by a multicomponent reaction of β-enaminonitriles, α,β-unsaturated aldehydes, and 2-aminothiol hydrochlorides

A wide library of 3,7,8,8a-tetrahydro-2 H-thiazolo[3,2- a]pyridines has been prepared by simple heating in acetonitrile of β-enaminonitriles, α,β-unsaturated aldehydes and 2-aminothiol hydrochlorides. Chemical yields depend on the nature, hindrance, and position of the substituents. The scope, limit...

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Bibliographic Details
Published in:Tetrahedron 2010-04, Vol.66 (15), p.2815-2822
Main Authors: Perrino, Mónica Pérez, Villar-Guerra, Rafael del, Sañudo, M. Carmen, Calvo, Luis A., González-Ortega, Alfonso
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocycles
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Multicomponent reaction
Organic chemistry
Preparations and properties
Thiazolo[3,2- a]pyridines
α,β-Unsaturated aldehydes
β-Enaminonitriles
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Summary:A wide library of 3,7,8,8a-tetrahydro-2 H-thiazolo[3,2- a]pyridines has been prepared by simple heating in acetonitrile of β-enaminonitriles, α,β-unsaturated aldehydes and 2-aminothiol hydrochlorides. Chemical yields depend on the nature, hindrance, and position of the substituents. The scope, limitations, and stereocontrol associated to this three-component reaction have been studied in detail. In general, the diastereoinduction observed in the three new stereogenic centers generated in the pro-chiral α,β-unsaturated aldehyde is low. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.02.051