2-Amino-4-dimethylamino-1-thia-3-azabutadienes as Precursors of Thiazoles

Abstract

The reaction of 2-amino-4-dimethylamino-1-thia-3-azabutadienes 1 with f -bromoketones gave rise to 2-aminothiazoles 2 together with 2-( N , N -dimethylaminomethylenamino)thiazoles 3 . Competitive mechanisms are described. Furthermore, reaction of diene 1a with methyl f -bromoacetate or hydroxylamine- O -sulfonic acid yielded respectively 2-( N , N -dimethylaminomethylenamino)thiazolin-4-one 4 and 5-amino-1,2,4-thiadiazole 5 .

Keywords:

• 2,4-Diamino-1-thia-3-azabutadienes
• 1,2,4-thiadiazole
• Thiazoles
• Thiazolin-4-one