1-Aryl-6-carboxy-1,2,4-triazine-3,5 (2H, 4H)-diones - prepd. from aryl- diazonium salts through a mesoxalyl diurethane and the 6-(N-carbethoxy)-carboxamido deriv of the final prod.

摘要

The title process is represented by:- Aryl-N2-Cl over right arrow malanydiurethane cyclisation hydrolysis (where Aryl is R4 R2 and R6 are H,F,Cl,CN or provided at least one is H or F; R3 and R5 are either (1) H, N,CF3, halogen or alkyl, (2) alkoxy or alkylthio or (3) NO2 or CNS; R4 is as R3 or R5 (1)-(3) or is (4) NR7R8 alkyl SO2, SO2NRR1 or alkanoyl provided that when R4 is SO2NRR1 or alkanoyl at least one of R3 and R5 is other than H and that when R3 and R5 is selected from (2) R4 is selected from (1), (3) or (4) and when R4 is H, Me, NO2 and at least one of R2 R3 R5 and R6 is other than H, R is Me, Et, alkyl, propargyl, phenyl, benzyl a p-chlorophenyl; R1 is Me, Et, Alkyl or propargyl or NRR1 may be morpholine, thiomorpholine, pyrrole, pyrroline, pyrrolidine, piperidine, N-alkylpiperazine, piperazine, hexamethylamine, 3,4-dichloropiperidine thiazolidine or DELTA 3-tetrahydropyridine R7 and R8 are 1-4C alkyl or NR7R8 is morpholine, thiomorpholine pyrrole, pyrroline, pyrrolidine, piperidine, N-alkylpiperazine hexamethyleneamine, thiazolidine, DELTA 3-tetra hydropyridine or piperazine, X is O, S > CO, NH, SO, SO2 or CHOH and Y and Y' are H, NO2 CN, halogen alkyl or alkoxy).