The Journal of Organic Chemistry

A new route to N-monosubstituted thioamides utilizing phosphoramidothionates as reagents for the thioamidation of carboxylic acids

KE DeBruin, EE Boros

Index: DeBruin, Kenneth E.; Boros, Eric E. Journal of Organic Chemistry, 1990 , vol. 55, # 25 p. 6091 - 6098

Full Text: HTML

Citation Number: 24

Abstract

Several N-monosubstituted thioamides have been synthesized from the corresponding carboxylic acid chlorides and primary amines by a new procedure. The procedure utilizes a commercially available and inexpensive organophosphorus reagent (dimethyl chlorothiophosphate) to derivatize the amine, form the carboxamide bond, and accomplish the thionation of the carbonyl by an intramolecular rearrangement. The phosphoryl group ...

Related Articles:

P 4 S 10/dimethicone tandem: efficient reagent for thionation of various aromatic amides and esters

[Cho, Dongho; Ahn, Jiyoung; De Castro, Kathlia A.; Ahn, Hyunseok; Rhee, Hakjune Tetrahedron, 2010 , vol. 66, # 30 p. 5583 - 5588]

Benzylic metallation of thiobenzamides and thionaphthamides

[Ach, David; Reboul, Vincent; Metzner, Patrick European Journal of Organic Chemistry, 2002 , # 15 p. 2573 - 2586]

A general method for the n-alkylation of thioamides.

[Katritzky, Alan R.; Drewniak, Malgorzata Tetrahedron Letters, 1988 , vol. 29, # 15 p. 1755 - 1758]

Efficient and Green Protocol for the Synthesis of Thioamides in C6 (mim) 2Cl2 as a Dicationic Ionic Liquid

[Khosropour; Noei; Mirjafari Journal of the Iranian Chemical Society, 2010 , vol. 7, # 3 p. 752 - 758]

New direct synthesis of thioamides from carboxylic acids

[Borthakur, Naleen Tetrahedron Letters, 1995 , vol. 36, # 37 p. 6745 - 6746]

More Articles...