A one-step, multi-component reaction for the synthesis of fully substituted 5-amino-4-carboxamidthiazoles

A one-step, multi-component reaction for the synthesis of fully substituted 5-amino-4-carboxamidthiazoles

[Display omitted] A novel multi-component reaction has been developed for the synthesis of fully substituted 5-amino-4-carboxamidthiazoles. Condensation of an aldehyde with commercially available 2-amino-2-cyanoacetamide in the presence of elemental sulfur and base affords these heterocycles in a on...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 54; no. 20; pp. 2506 - 2510
Main Authors: Childers, Kaleen K., Haidle, Andrew M., Machacek, Michelle R., Rogers, J. Patrick, Romeo, Eric
Format: Journal Article
Language:English
Published: Elsevier Ltd 15-05-2013
Subjects:
Aldehydes
Aliphatic compounds
Aromatic compounds
Condensing
Gewald reaction
Multi-component reaction
Sulfur
Synthesis (chemistry)
Tetrahedrons
Thiazole
Thiazole
Gewald reaction
Multi-component reaction
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Summary:[Display omitted] A novel multi-component reaction has been developed for the synthesis of fully substituted 5-amino-4-carboxamidthiazoles. Condensation of an aldehyde with commercially available 2-amino-2-cyanoacetamide in the presence of elemental sulfur and base affords these heterocycles in a one-pot reaction sequence. A variety of aryl, heteroaryl, and aliphatic aldehydes were successfully utilized, thus providing rapid access to functionalized thiazoles that are valuable intermediates in the synthesis of pharmacologically active compounds.
Bibliography:ObjectType-Article-1
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.03.014