Synthesis and reactions of new triazino thiadiazino and pyrimido thieno[2,3-b]-quinoxaline

3-Amino-2-carbamoylthieno[2,3-b]quinoxaline 3 was synthesized and allowed to react with chloroacetyl chloride to give N-chloroacetyl derivative 4. Cyclization of 4 into the title compund 5 was achieved in boiling acetic anhydride. Reactions of 5 with morpholine and diethylamine afforded pyrimidinones 6 and 7. Reaction of 3 with sulfuryl chloride, thionyl chloride and nitrous acid gave thiadiazine derviatives 8 and 9 and triazinothienoquinoxaline 11. Thionation and chlorination of 11 by P2S5 and/or POCl3 gave thioxotriazino and chlorotriazinothienoquinoxalines 12 and 13, respectively. Treatment of either 12 or 13 with hydrazine hydrate afford the hydrazinotriazinoquinoxaline 14 which was utilized as precursor for producing other new triazinothienoquinoxalines 15-17.