Mechanistic Study of a Complementary Reaction System that Easily Affords Quinazoline and Perimidine Derivatives

作者：Wang Zerong Daniel^*; Eilander Joshua; Yoshida Motoko; Wang Tianzhi

来源：European Journal of Organic Chemistry, 2014, 2014(34): 7664-7674.

DOI：10.1002/ejoc.201402854

• Synthetic methods
• Nitrogen heterocycles
• Solvent effects
• Reactive intermediates
• Reaction mechanisms

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 -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.

• 出版日期2014-12