Novel heterocyclics from 3-substituted-5H-1,2,4-triazino-[5,6-b]indoles and π-acceptors

Article abstract of DOI:10.1016/S0040-4020(01)89615-0

The reaction of 1,2,4-triazino[5,6-b]indole-3-thione 1 with tetracyanoethylene (TCNE) afforded the disulfide 6, the tricyanovinylation product 8 and thiazolotriazinoindole 11. 3-Aryl-5H-1,2,4-triazino[5,6-b] indoles 2a,b reacted with TCNE to give pentacyanopropene 12 and 3-aminotriazinoindole derivatives 14a,b. 3-Hydrazino-5H-1,2,4-triazino[5,6-b]indole 3 reacted with TCNE, dicyanomethyleneindane-1,3-dione (CNIND) and 2,3-dicyano-1,4-naphthoquinone (DCNQ) to form triazolotriazinoindoles 17 and the triazepinotriazinoindoles 16,24 and 26. The reaction of 3 with chlorinated quinones gave the quinazolinetriones 21-23.