Efficient Uncatalyzed Conversion of Primary and Secondary Thioamides into 1-Substituted, 5-Substituted, 1, 5-Disubstituted and Annulated Tetrazoles

AAS El-Ahl, FA Amer, AH Elbeheery

Index: El-Ahl, Abdel-Aziz S.; Amer, Fatty A.; Elbeheery, Akram H. Phosphorus, Sulfur and Silicon and the Related Elements, 2011 , vol. 186, # 11 p. 2226 - 2235

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Abstract

Abstract Unprecedented high-yield simple and mild conversion of primary aliphatic and aromatic thioamides into 5-substituted tetrazoles on treatment with a combination of tetrachlorosilane and sodium azide in refluxing acetonitrile has been achieved. Secondary acyclic, cyclic, and heterocyclic thioamides could also be transformed in high yields into 1- substituted, 1, 5-disubstituted, or annulated tetrazoles under the same reaction condition. ...

~91%

~94%

~88%

~86%

~89%

~84%

~94%

~79%

~89%

~88%

~82%

~91%

~92%

~90%

1, 3??Dipolar Cycloaddition: Click Chemistry for the Synthes...

[Aureggi, Valentina; Sedelmeier, Gottfried Angewandte Chemie - International Edition, 2007 , vol. 46, # 44 p. 8440 - 8444]

A novel approach for the synthesis of 5-substituted tetrazol...

[El-Ahl, Abdel-Aziz S.; Elmorsy, Saad S.; Elbeheery, Akram H.; Amer, Fathy A. Tetrahedron Letters, 1997 , vol. 38, # 7 p. 1257 - 1260]