Reaction of 2-aminobenzamide analogs and 2-aminothiophenol with ethyl 3-ethoxymethylene-2,4-dioxovalerate. Synthesis of pyrrolo[1,2-α]quinazoline and pyrrolo[1,2-a]benzothiazoline derivatives

The reaction of ethyl 3-ethoymethylene-2,4-dioxovalerate (EMDV) ( 1 ) with 2-aminobenzamide ( 2 ), 2-aminobenzthioamide ( 3 ), 2-aminobenzmethylamide ( 4 ) and 3-amino-2-methyl- or phenylpyrazole-4-carbox-amides ( 6 and 7 ) produced ethyl 3-aminomethylene-2,4-dioxovalerates ( 10, 15, 16, 18 and 19 ), which led to pyrrolo1,2-a]quinazoline-1,5-diones ( 11, 22 and 23 ) and pyrrolo1,2-a]pyrazolo4,3-e]pyrimidine-1,5-diones ( 24 and 25 ) under the acidic condition, respectively. Analogously, 2-aminothiophenol reacted with 1 to give 21 , which was subsequently derived to pyrrolo1,2-a]benzothiazolin-l-one ( 26 ) under the neutral condition. Furthermore, we prepared the heterocyclic steroidal molecules ( 41, 43, 45, 47, 49 and 51 ) by condensation of 11 and 26 with hydrazine, methylhydrazine and phenylhydrazine.