54968-60-4

Usage

InChI:InChI=1/C10H10N2O3S2/c1-4-5(2)17-9-7(4)8(15)11-10(12-9)16-3-6(13)14/h3H2,1-2H3,(H,13,14)(H,11,12,15)/p-1

Upstream product

• 38201-64-8 5,6-dimethyl-2-thioxo-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one 
• 79-11-8 chloroacetic acid 
• 53162-53-1 ethyl 4,5-dimethyl-2-(3-benzoylthioureido)-3-thiophenecarboxylate 
• 4815-24-1 2-amino-4,5-dimethyl-3-thiophenecarboxylic acid ethyl ester 
• 60442-34-4 2-(2-chloro-acetylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester 
• 333-20-0 potassium thioacyanate 
• 53162-51-9 2-thio-4-oxo-5,6-dimethyl-3,4-dihydrothieno<2,3-d>pyrimidine potassium salt 
• 64-69-7 Iodoacetic acid 

Relevant academic research and scientific papers

New syntheses of 2-alkylthio-4-oxo-3,4-dihydroquinazolines, 2-alkylthioquinazolines, as well as their hetero analogues

N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-4-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with amines.