6- Chloro-2 -quinoxalinone

Chloro-l-methyl-2-quinoxalinone (215), which cannot anionize, reacts readUy with iV -methylaniline. 6-Bromo-as-triazine-3,5-dione (216) is largely anionized by dimethylamine but not by thiourea... [Pg.248]

Chloro-3- [(1 -ethoxycarbonyl-1 -methylethyl)amino] -4-nitrobenzene (61) gave 6-cbloro-3,3-dimetbyl-3,4-dibydro-2(lF/)-quinoxalinone (62) (TiCl3, AcONa,... [Pg.11]

Chloro-l,2-benzenediamine (137) and glyoxylic acid gave a mixture of 6-chloro- (138) and 7-chloro-2(l//)-quinoxalinone (139) from which only 6-isomer could be isolated in a pure state (OHCCO2H, H20-Me0H, 20°C, 24h 37%). ... [Pg.22]

Benzenediamine (148) and frani-l-chloro-l,2-bis(hydroxyimino)ethane (149) gave 2(177)-quinoxalinone oxime (150), perhaps better formulated as 2-hydroxyaminoquinoxaline (151) (EtOH, 20°C, 3 h 71%) 6,7-dibromo-l,2-benzenediamine likewise gave 6,7-dibromo-2-hydroxyamino-quinoxaline. ... [Pg.24]

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]

Only one procedure has been reported recently within this category. Thus 7-chloro-l-methyl-5-phenyl-2,3-dihydro-lH-benzodiazepin-2-one 4-oxide (437) with dimethyl acetylenedicarboxylate in methylene chloride at 20° C for 3 days gave a separable mixmre of the primary tricyclic adduct, dimethyl lO-chloro-6-oxo-llb-phenyl-5,6,7, 1 lb-tetrahydroisoxazolo[2,3-t/] [ l,4]benzodiazepine-1,2-dicarboxylate (438), and its rearrangement product, 6-chloro-4-(2-methoxalyl-2-methoxycarbonyl-l-phenylvinyl)-l-methyl-3,4-dihydro-2(lT0-quinoxalinone (439) each product afforded 6-chloro-l-methyl-2(l//)-quinoxalinone (440) on refluxing in ethanol (see also Section 1.7.13). However, the final quinoxaline (440) was best obtained in 75% yield) by simply heating the initial substrate (437) and dimethyl... [Pg.59]

Ethyl 10-chloro-7-methyl-6-oxo-l lb-phenyl-5,6,7,1 lb-tetrahydroisoxazolo[2, 3- /][l,4]benzodiazepine-l-carboxylate (563) gave a separable mixture of 6-chloro-4-(2-ethoxycarbonyl-2-formyl-l-phenylvinyl)-l-methyl-3,4-dihy-dro-2(17/)-quinoxalinone (564), 4-(2-benzoyl-2-ethoxycarbonylvinyl)-6-chloro-1-methyl-3,4-dihydro-2(l//)-quinoxalinone (565), and 6-chloro-l-methyl-3,4-dihydro-2(l//)-quinoxalinone (567) (EtOH, reflux, 21 h 2%, 8%, and 20%, respectively, after separation structures 564 and 565 were... [Pg.77]

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]

Dimethoxy-3-phenyl-2(l/7)-quinoxalinone gave 2-chloro-5,7-dimethoxy-3-phenylquinoxaline (4) (POCI3, reflux, 30 min 94%) " 6,7-dimethoxy-2,3(1//,4//)-quinoxalinedione gave 2,3-dichloro-6,7-dimethoxyquinoxaline (5) (POCI3, 100°C, 4h 83%)J ... [Pg.134]

Chloro-l-methyl-2,3(l//,4/i)-quinoxalmedione (6) gave 3,6-dichloro-l-methyl-2(l//)-quinoxalinone (7) (POCI3, reflux, 90 min 74% note immunity of... [Pg.134]

Methyl-6-nitro-2(l//)-quinoxalinone gave the 2-chloro-3-methyl-6-nitroqui-noxaline (12) (POCI3, PhNMe2, reflux, 2h 86%). ... [Pg.135]

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-3-[p-(l-ethoxycarbonylethyl)phenoxy]quinoxaline (127) gave 7-chloro-3- [p-( 1 -ethoxycarbonylethyl)phenoxy] -2( l//)-quinoxalinone (128),... [Pg.157]

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]

Acetonyl-2(l//)-quinoxalinone (231, R = Me) reacted as its tautomer (231a, R = Me) to give 2-chloro-3-(2-chloroprop-l-enyl)quinoxaline (232, R = Me) (POCI3, pyridine, reflux, 10 min 62%) 3-phenacyl-2(l//)-quinoxalinone (231, R = Ph) likewise gave 2-chloro-3-(p-chlorostyryl)quinoxaline (232,... [Pg.174]

Azido-6-chloroquinoxaline 4-oxide (22, R = N3) gave 3-azido-7-chloro-2(lT0-quinoxalinone (23, R = N3) (AC2O, AcOH, reflux, 4 h 46%) " ° 6-chloro-2-piperidinoquinoxaline 4-oxide [22, R = N(CH2)s] gave 7-chloro-3-piperidino-2(177)-quinoxalinone [23, R = N(CH2)5](likewise 58%)." °... [Pg.192]

Methoxycarbonylmethyl-2(l//)-quinoxalinone (220) with p-chlorobenzene-diazonium chloride gave a product, initially formulated as 3-[a-(p-chloro-phenylazo)-a-methoxycarbonylmethylene]-3,4-dihydro-2(l//)-quinoxalinone (221) but later as the tautomeric 3-[a-(p-chlorophenyUiydrazono)-a-methoxy-carbonylmethyl]-2(l//)-quinoxalinone (222) (HCl, H2O, AcOH, <5°C, 10 min, then 95°C, 30 min 90%). ° Such tautomerisms have been studied in some detail.(See also Section 6.6.)... [Pg.299]

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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