1.3- Dimethyl-5,6,7,8-tetrahydro-4 cinnolinone

Dimethyl-l,3-cyclohexanedione (dimidone, 145) and ethyl 2-(/7-tolylhydra-zono)acetoacetate (146) gave ethyl 4,7,7-trimethyl-5-oxo-l-p-tolyl-l,5,6,7-tetrahydro-3-cinnohnecarboxylate (147) (neat AcONEU, 170°C, 30 min 80%) " the same substrate (145) and benzil monohydrazone (148) gave 7,7-dimethyl-3,4-diphenyl-6,7-dihydro-5(l//)-cinnolinone (149) (or tauto-... [Pg.22]

Acetoxy-2-methyl-2,3,4,5,6,7-hexahydrobenzofuran-3-one (170) with hydrazine gave 3-methyl-5,6,7,8-tetrahydro-4(l//)-cinnolinone (171) (EtOH, 20°C, 12 h 85%) or with methylhydrazine gave a separable mixture of 1,3-dimethyl-5,6,7,8-tetrahydro-4(17/)-cinnolinone (172) and 2,3-dimethyl-5,6, 7,8-tetrahydrocinnolin-2-ium-4-olate (173) (EtOH, 0°C 20°C, 12 h 67% and 15%, respectively) the related substrate, 2-methoxy-2-methyl-... [Pg.25]

C0CH2C1), 7,7-dimethyl-3-phenyl-4,6,7,8-tetrahydro-5( l//)-cinnolinone tautomer), and 2-ethoxycarbonyImethy 1-2,3-dihydro-4(l//)-cinnoli-also 6-lluoro- and 7-methyl-4-oxo-l,4-dihydro-3-cinnolinecarboxylic... [Pg.60]

C, h > 50%) and thence l,2-bis(chloroacetyl)-6,7-dimethyl-2,3-dihydro-4(l/f)-cinnolinone (54) (CICH2COCI, EtaN, see original for details) 2,3-dihydro-4(177)-cinnolinone (52, R = H) with 3-chloropropionyl chloride gave 2,3,5,6-tetrahydro-17/-pyrazolo[l,2-fl]cinnoline-3,6-dione (55) as the final product (PhH, reflux, 10 h 54%) " also another A -acylation. ... [Pg.67]

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