Behaviour of hexahydrobenzodipyrazolones towards chloroacetylation, aminoalkylation, Grignard reagent and their antimicrobial activity

Treatment of 2,3a,4,6,7a,8-hexahydrobenzo 1,2-c; 4,5-c] dipyrazole-3,7-dione (1) with chloroacetyl chloride gave the 2,6-bis (chloroacetyl) derivative (2), which on treatment with acetic anhydride pyridine afforded (3). Compound (2) when heated with pyridine afforded (1). Compound (1) underwent Mannich reaction with piperidine or morpholine and formaldehyde to give the 2,6-bis (piperidino or morpholinomethyl) derivatives (4a,b). Hydroxymethylation of (1) with formaldehyde gave the 2,6-bis (hydroxylmethyl) derivative (4), which on heating with piperidine afforded (4a), Reaction of 2,3a,4,6,7a,8-hexahydro- 2,6-bis (phenylsulphonyl) benzo 1,2-c; 4,5-?] dipyrazole-3,7-dione (7) with phenylmagnesium bromide gave dodecahydro-3,3,4a,7,7,8a-hexaphenyl-2,6- bis (phenylsulphonyl) benzo 1,2-c; 4,5-?] dipyrazole (8). Derivatives of hexahydrobenzodipyrazolone (9a-g) have been subjected to general screening for their antimicrobial activity.