S. Sunder, N. Peet
Nov 1, 1979
Citations
0
Influential Citations
8
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Isatoic anhydride (1a) and 5-chloroisatoic anhydride (1b) were treated with 2-(1-methylhydrazino)ethanol (2) to produce 2-aminobenzoic acid 2-(2-hydroxyethyl)-2-methylhydrazide (3a) and its 5-chloro analog 3b, respectively. Treatment of 3a and 3b with carbon disulfide gave, respectively, 2,3-dihydro-3-[(2-hydroxyethyl)methylamino]-2-thioxo-4-(1H)quinazolinone (4a) and its 6-chloro analog 4b. Compounds 4a and 4b afforded 5,6-dihydro-5-methyl-2-thioxo-4H,8H-[1,3,5,6]oxathiadiazocino[4,5-b]quinazolin-8-one (5a) and its 10-chloro analog 5b, respectively, upon treatment with thiophosgene. Compound 5a could be produced directly from 3a and thiophosgene. Treatment of 4a and 4b with trifluoroacetic anhydride followed by potassium carbonate gave 3,4-dihydro-4-methyl-2H,6H-[1,3,4]thiadiazino[2,3-b]quinazolin-6-one (7a) and its 8-chloro analog 7b, respectively. Treatment of 4a with thionyl chloride also gave 7a, but 4b and thionyl chloride afforded a mixture of 7b and 8-chloro-3,4-dihydro-4-methyl-2H,6H-[1,3,4]oxadiazino[2,3-b]quinazolin-6-one (10). The dimethyl analogs of 4a and 4b (13a and 13b) upon treatment with thiophosgene afforded 3,4-dihydro-2,2,4-trimethyl-2H,6H-[1,3,4]oxadiazino[2,3-b]quinazolin-6-one (14a) and its 8-chloro analog 14b, respectively.