193-04-4Relevant academic research and scientific papers
Mechanistic study of a complementary reaction system that easily affords quinazoline and perimidine derivatives
Wang, Zerong Daniel,Eilander, Joshua,Yoshida, Motoko,Wang, Tianzhi
, p. 7664 - 7674 (2014)
A new reaction between 2-aminobenzophenone and thiourea in dimethyl sulfoxide (DMSO) has been developed that primarily affords 4-phenylquinazoline as a single product. This reaction is also applicable, in general, to the reactions between thiourea and conformation-restricted β-amino ketones, such as 1-aminoanthracene-9,10-dione and 1-amino-9H-fluoren-9-one, to prepare perimidine derivatives. Experimental data is consistent with our computational study on the thermal decomposition of thiourea to form hydrogen sulfide and carbodiimide. This reaction involves a coupling between 2-aminobenzophenone and carbodiimide generated in situ from thiourea to form 4-phenylquinazolin-2(1H)-imine intermediate, and the generation of sulfur-containing reducing agent from hydrogen sulfide and DMSO, which reduces 4-phenylquinazolin-2(1H)-imine to 4-phenyl-1,2-dihydroquinazolin-2-amine. Elimination of ammonia from the latter yields 4-phenylquinazoline.
