3-Phenyl-4 -cinnolinone

In contrast, the same substrate (93) under less gentle conditions gave only 3-phenyl-4(lH)-cinnolinone (95), presumably via the initial product (94, X = Cl) (36% HCl, NaNOji slowly, 0°C, 2h then reflux, 1 h 82%). l-(o-Aminophenyl)-2-trimethylsilylacatylene (96) gave 4(l//)-cinnolinone (97) (6M HCl, NaN02i slowly, <0°C, 30 min then reflux, 3h 73%). ... [Pg.15]

Trimethyl-6-phenacyl-l,4-benzoquinone (98) gave 5,7,8-trimethyl-3-phenyl-6(2//)-cinnolinone (99) (H2NNH2 H2O, trace AcOH, PhMe, 20°C,... [Pg.15]

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]

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]

Bromo-l-phenyl-7-(pyridin-4-yl)-4(l//)-cinnolinone (46, R = Br) gave 4-oxo-l-phenyl-7-(pyridin-4-yl)-l,4-dihydro-3-cinnolinecarbonitrile (46, R = CN) (CuCN, MeaNCHO, reflux, 18 h crude nitrile), characterized by conversion into 4-0X0- l-phenyl-7-(pyridin-4-yl)-1,4-dihydro-3-cinnolinecarboxylic acid (46, R = C02H) (50% H2SO4, 110°C, 12 h 33% overall). ... [Pg.52]

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]

Phenyl-5,6-dihydro-3(2//)-cinnolinone (21, R = H) gave 2-ethoxycarbonyl-methyl-7-phenyl-5,6-dihydro-3(2//)-cinnolinone (21, R = CH2C02Et) (Et02-CCHjBr, K2CO3, AcMe, reflux, 24 h 40%). ... [Pg.62]

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]

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]

This unusual transformation is exemplified in the isomerization of l-(o-methoxy-carbonylbenzoyl)-l,4-dihydro-3(2f/)-cinnolinone (189) into 2-[o-(methoxycarbonyl-methyl)phenyl]-l,4(2//,3//)-phthalazinedione (190) by refluxing in methanolic sulfuric acid or aqueous methanolic potassium hydrogen carbonate for 90 min or 7 h, respectively yields were unstated. ... [Pg.141]

Chloro-3-phenyl-4(l/7)-cinnolinone 4-Chloro-3-phenylethynylcinnoline 3-Chloro-4-(A -phenyUiydrazino)cinnoline... [Pg.359]

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