5.6.7.8- Tetrahydro-3 -cinnolinone

On reduction with LAH, cinnolines generally yield di- and tetrahydro derivatives. The LAH reduction of 5,6,7,8-tetrahydro-3-cinnolinones (304) in THF leads to mixtures of the dihydrocinnolines 305, the decahydro cinnolines 306 and the deoxygenated tetrahydrocinnolines 307. The ratio of products is dependent on the substituents and the amount of LAH used. ... [Pg.51]

Ethoxycarbonylmethyl)cyclohexane (100) gave 4,4a,5,6,7,8-hexahydro-3 (27/)-cmnolinone (101) (H2NNH2 H2O, EtOH, reflux, 1 h 72%) and thence 5,6,7,8-tetrahydro-3(2f/)-cinnolinone (102) (CuCl2, MeCN, reflux, 1 h 87%) minor variations in the foregoing reaction produced lower yields. ... [Pg.16]

In contrast, 2-(a-carboxy-a-morpholinomethyl)cyclohexanone, as its morpholi-nium salt (103), gave 5,6,7,8-tetrahydro-3(2/i)-cinnolinone (102) directly oxidation was provided by spontaneous loss of morpholine (H2NNH2 H2O,... [Pg.16]

Phenacyl-l,3-cyclohexanedione (106) gave 3-phenyl-4,6,7,8-tetrahydro-5(lfl)-cinnolinone (107 unisolated) and thence 3-phenyl-5,6,7,8-tetrahydro-5-cin-nolinone (108) by oxidation (H2NNH2, EtOH, 20°C, 30 min then dichloro-... [Pg.16]

Carboxymethyl-5-phenylcyclohex-5-enone (109) gave 7-phenyl-4,4a,5,6-tet-rahydro-3(2//)-cinnolmone (110, R = H) (neat H2NNH2-H20, reflux, 4h 92%) or 2-methyl-7-phenyl-4,4a,5,6-tetrahydro-3(27/)-cinnolinone (110, R = Me) (H2NNHMe, EtOH, reflux, 16 h 65%) analogs likewise. ... [Pg.17]

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]

Tetrahydro-l-benzazocine-2,6(l/i)-dione (168) gave 3-(2-carboxyethyl)-4(l//)-cinnolinone (169) (MeOCHzCHzOMe, trace HjO, BuONO, HCl gasi, 25 C, 5 min then stirred, 25°C, 12 h then suspension of crude diazonium intermediate, lOO C, 5 min 61%) a dozen analogs, substimted in the phenyl... [Pg.25]

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]

Cinnoline (18) gave 3-chlorocinnoline (neat POCI3, reflux, 10 days 91%) ° ° the reduced substrate, 5,6,7,8-tetrahydro-3(2//)-cinnolinone (19), likewise gave 3-chloro-5,6,7,8-tetrahydrocinnoline (neat POCI3, 100°C, until substrate dissolved 20%). ... [Pg.49]

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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