3- -quinoxalinone analog

Aminopyrazines and 2-aminoquinoxalines, like their pyridine analogs, react with nitrous acid under aqueous conditions to give the 2(l//)-pyrazinones and 2(l//)-quinoxalinones. 2-Aminoquinoxalines are more readily hydrolyzed than typical heterocyclic amines and 2-amino-3-methylquinoxaline, for example, undergoes hydrolysis on heating at 100 °C with dilute sodium hydroxide (59JCS1132). [Pg.177]

Acetamido-5-methoxy-1,2-benzenediamine (prepared in situ by reduction of 1 -acetamido-2-methoxy-4,5-dinotrobenzene) gave 6-acetamido-7-methoxy-quinoxaline (104) (OHCCHO-2NaHS03 H20, 70°C, 2 h 96%). 4-Acetamido-2,3-diaminophenol (105) (prepared in situ by reduction of the 2,3-dinitro analog) gave 8-acetamido-5(l//)-quinoxalinone (106) (OHCCHO-2NaHS03-H20, reflux, Nji, 2 h 79%). °... [Pg.17]

In contrast, 4-methyl-1,2-benzenediamine (263) and the same synthon (261) gave an inseparable 70 30 mixture of 3-amino-7-methyl- (264) and 3-amino-6-methyl-2(177)-quinoxalinone (265) [EtOH, 25°C, >8 h 77% (mixture)] likewise analogous mixtures. [Pg.38]

Benzenediamine (277, R = H) and ethyl 2-chloro-2-(phenylhydrazono)ace-tate (280) gave 3-(2-phenylhydrazino)-2(l/f)-quinoxalinone (281) (Et3N, EtOH, reflux, 3 h 72) analogs likewise. ... [Pg.39]

An analogous substrate, dimethyl 10-chloro-7-methyl-6-oxo-l lb-phenyl-5,6,7,1 lb-tetrahydroisoxazolo[2,3-d][l,4]benzodiazepine-l,2-dicarboxylate (566), gave not 567 but 6-chloro-l-methyl-2(l/7)-quinoxalinone (EtOH, reflux, 30 h -40%). ... [Pg.77]

Methyl-2(l//)-quinoxalinone (138) gave 3-(3-benzoylacetonyl)-2(17/)-quinox-alinone (139) [LiNPr 2 (made in situ), THF, reflux—>20°C, 90 min then BzCH2C02Et, 20°C, 2h 91%] several analogs like 3-nicotinoylmethyl-... [Pg.117]

Methoxycarbonylmethyl-1 -methyl-2( 177)-quinoxalinone gave 3-[a-methoxy-carbonyl-a-(p-tolylhydrazono)methyl]-l-methyl-2(177)-quinoxalinone (171) [ i-MeCcH4N20Ac (prepared in situ), ACOH-H2O, 20°C 95°C, 1 h 36%] " analogous esters likewise." " ... [Pg.123]

Chloro-l-methyl-2(l//)-quinoxalinone (120) gave 3-(// -ethoxycarbonylhy-drazino)-l-methyl-2(l//)-quinoxalinone (121) (EtOaCNHNHa, MeCN, 120°C, sealed , 2h %) analogs likewise. ... [Pg.156]

Dichloro-l-methyl-2(lf/)-quinoxalinone (173, R = C1) gave 3-azido-6-chloro-l-methyl-2(l//)-quinoxalinone (173, R = N3) (NaNs, Mc2NCHO, 120°C, 90 min 96%) analogs Ukewise. ... [Pg.165]

Bromomethyl-l-methyl-2(l//)-quinoxalinone (268, R = Br) gave l-methyl-3-phenoxymethyl-2(17/)-quinoxalinone (268, R = OPh) (PhOH, NaOH, Me3PhCH2NCl, CHCI3-H2O, 50°C, tic monitored 41% analogs like-wise). 5... [Pg.181]

Bromo-7-fluoro-3,4-dihydro-2(177)-quinoxalinone (35) gave 6-bromo-7-fluoro-5-nitro-2,3(177,477)-quinoxalinedione (36) regioselectively (fuming HNO3, F3CCO2H, 20°C, 12 h 85% analogs likewise). ... [Pg.193]

Note These typical examples include both intra- and intermolecular cychza-tions, some of which do not directly involve the 0x0 substiment. 3-(a-Bromophenacyl)-2(l//)-quinoxalinone (102) gave 3-bromo-2-phenylfuro-[2,3-h]quinoxaline (103) (95% H2SO4, 65°C, 4 h 90% analogs likewise) a... [Pg.204]

Methyl-2(17/)-quinoxalinone (109) and 2-methylacrylonitrile (110) gave the photoadduct, l,2a-dimethyl-3-oxo-2,2a,3,4-tetrahydro-l//-azeto[ 1,2-u]quinoxa-line-l-carbonitrile (111) (CH2CI2, MeOH, hv, N2, <15 h >95%) also analogs using significantly electron-deficient olefines. [Pg.205]

Methyl-3-(2,3,4-trihydroxy- l-phenyUiydrazonobutyl)-2( 1 //)-quinoxalinone (186) gave 3-(5-acetoxymethyl-1 -phenylpyrazol-3-yl)-1 -methyl-2( 1 //)-qui-noxahnone (187) (neat AC2O, reflux, 3 min 80% note additional acetyla-tion) ° also analogous cyclizations. ... [Pg.218]

Methyl-2(17/)-quinoxalmone (215) gave l-benzenesulfonyl-3-methyl-2(17/)-quinoxalinone (216) (PhS02Cl, K2CO3, AcMe, reflux 3 h 90% analogs likewise). [Pg.223]

Fluoro-2(17/)-quinoxalinone 4-oxide (273) gave 6-fluoro-3-methyl-2(l//)-quinoxalinone (275), probably by degradation of the adduct (274) (ACCH2-COjEt, PhH, H2O, NaOH, 65°C, 1 h % several analogs likewise). ... [Pg.236]

Amino-3-phenyl-3,4-dihydro-2(177)-quinoxalinone (181) and triphosgene gave 4-phenyl-47/-imidazo[l,5,4-< e]quinoxaline-2,5(l//, 6//)-dione (182) (EtsN, THF, 20°C, N2, until substrate gone by tic 65%) analogs Ukewise. ... [Pg.293]

Chloro-2,2-dimethyl-3-oxo-1,2,3,4-tetrahydro-1 -quinoxalinecarbonyl chloride (89) gave 6-chloro-4-(3,5-dimethylpiperazin-l-yl)carbonyl-3,3-dimethyl-3,4-dihydro-2(177)-quinoxalinone (90) [substrate, EtPr N, CH2CI2 HN(CH2-CHMe)2NHi, 0°C 20°C, 17 h 54%] analogs likewise. " ... [Pg.334]

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