3- Acetyl-6- cinnolinone

Acetyl-1,4,4-triphenyl-l,2-diazetidin-3-one (162) rearranged into 2-acetyl-4,4-diphenyl-l,4-dihydro-3(2ff)-cinnolinone (163) (neat F3CCO2H >95% ... [Pg.24]

Trimethyl-3-phenyl-6(27/)-cinnolinone (50) gave 6-acetoxy-5,7,8-trimethyl-3-phenylcinnoline (51) (no details except NMR that does not preclude A-acetylation). ° ... [Pg.66]

Dimethyl-2,3-dihydro-4(l//)-cinnolinone (52, R = Me) gave 2-chloro-acetyl-6,7-dimethyl-2,3-dihydro-4(lfl)-cinnolinone (53) (CICH2CCXII, H2O,... [Pg.66]

H)-Cinnolinone (67, R = H) with lead tetracetacte in acetic acid did not imdergo O- or 7V-acetylation but oxidative C-acetoxylation to afford... [Pg.69]

Methylsulfinyl-4(l/i)-cumoIinone (12) gave 3-acetoxymethylthio-4(l//)-cinnolinone (11) (neat AC2O, reflux, 4h 65% by a Pummerer-type reaction and additional acetylation) or 4-chloro-3-chloromethylthiocinnoline (13) (neat SOCI2, reflux, 6h 92% note additional chlorolysis). ... [Pg.81]

Acetyl-6-(p-nitrophenylthio)-4(l//)-cinnolinone (14) gave 3-acetyl-6-(p-nitro-phenylsulfonyl) (l//)-cinnolinone (14a) (substrate, AcOH, 30% H202i... [Pg.82]

Acetyl-4(lfl)-cinnolinone (21) unexpectedly gave 3-acetyl-1-phenylazo-4(l//)-cinnolinone (22a) [substrate, Na2C03, EtOH, H2O PhN2Cl (fresh solution) slowly, < 5°C 95%] analogous substituted-phenylazo analogs likewise. However, the product (22a) was later reformulated as 3-phenyl-... [Pg.89]

Acetyl-4(l//)-cinnolinone (59) underwent cyclocondensation with malononi-trile to give 4-methyl-2-oxo-l,2-dihydropyrido[3,2-c]cinnoline-3-carbonitrile (58) (EtOH, trace piperidine, reflux, 2 h 65%) or, with ethyl cyanoacetate, to give 4-methyl-2-oxo-2//-pyrano[3,2-c]ciimoline-3-carbonitrile (60) (neat reactants, 165°C, 5h 70%). The same substrate (59) gave its tMosemi-carbazone (61) (H2NNH2CSNH2, AcOH, reflux, 2 h 70%), which underwent... [Pg.106]

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