4-chloro-3,5-dioxo

Piperidine, 3-aryIoxymethyI-4-phenyI-as antidepressant, 1, 169 Piperidine, JV-bromo-photoelectron spectroscopy, 2, 142 Piperidine, cis-4- t-butyl-r- cyclohexyl-1 -phenyl-X-ray analysis, 2, 161 Piperidine, 3-chloro-pyrrolidines from, 4, 147 Piperidine, N-chloro-photoelectron spectroscopy, 2, 142 reactions, 2, 373 trimerization, 3, 510 Piperidine, 4-cycIopentyI-2,6-dioxo-synthesis... 

Purines, N-alkyl-N-phenyl-synthesis, 5, 576 Purines, alkylthio-hydrolysis, 5, 560 Mannich reaction, 5, 536 Michael addition reactions, 5, 536 Purines, S-alkylthio-hydrolysis, 5, 560 Purines, amino-alkylation, 5, 530, 551 IR spectra, 5, 518 reactions, 5, 551-553 with diazonium ions, 5, 538 reduction, 5, 541 UV spectra, 5, 517 Purines, N-amino-synthesis, 5, 595 Purines, aminohydroxy-hydrogenation, 5, 555 reactions, 5, 555 Purines, aminooxo-reactions, 5, 557 thiation, 5, 557 Purines, bromo-synthesis, 5, 557 Purines, chloro-synthesis, 5, 573 Purines, cyano-reactions, 5, 550 Purines, dialkoxy-rearrangement, 5, 558 Purines, diazoreactions, 5, 96 Purines, dioxo-alkylation, 5, 532 Purines, N-glycosyl-, 5, 536 Purines, halo-N-alkylation, 5, 529 hydrogenolysis, 5, 562 reactions, 5, 561-562, 564 with alkoxides, 5, 563 synthesis, 5, 556 Purines, hydrazino-reactions, 5, 553 Purines, hydroxyamino-reactions, 5, 556 Purines, 8-lithiotrimethylsilyl-nucleosides alkylation, 5, 537 Purines, N-methyl-magnetic circular dichroism, 5, 523 Purines, methylthio-bromination, 5, 559 Purines, nitro-reactions, 5, 550, 551 Purines, oxo-alkylation, 5, 532 amination, 5, 557 dipole moments, 5, 522 H NMR, 5, 512 pJfa, 5, 524 reactions, 5, 556-557 with diazonium ions, 5, 538 reduction, 5, 541 thiation, 5, 557 Purines, oxohydro-IR spectra, 5, 518 Purines, selenoxo-synthesis, 5, 597 Purines, thio-acylation, 5, 559 alkylation, 5, 559 Purines, thioxo-acetylation, 5, 559... 

Substituents in the 6-position (cf. 267) show appreciable reactivity. 6-Bromo-as-triazine-3,5(2j, 4j )-dione (316) undergoes 6-substitution with secondary amines or hydrazine, with mercaptide anions or thiourea (78°, 16 hr), with molten ammonium acetate (170°, 24 hr, 53% yield), and with chloride ion during phosphorous oxychloride treatment to form 3,5,6-trichloro-as-triazine. The latter was characterized as the chloro analog of 316 by treatment with methanol (20°, heat evolution) and hydrolysis (neutral or acid) to the dioxo compound. The mercapto substituent in 6-mercapto-as-triazine-3,5(2iI,4if)-dione is displaced by secondary... 

Reaction of 2,4-dichloro-l,5-naphthyridine with ammonia (170°, 20 hr), hydrazine (100°, 16 hr), or aqueous hydrochloric acid (100°, 3 hr) was shown to yield the 2-amino- (47% yield) and 2-hydroxy-4-chloro derivatives (66% yield), but 2-hydrazino substitution (68% yield) was assumed. Disubstitution with ammonia (190°, 4 hr), hydrazine (100°, 48 hr), and ammonia-phenol (180°, 6 hr) occurred in high yield. Displacement of the 4-oxo group in 2,4-dioxo-l,5-naphthyridine occurs with aniline plus its hydrochloride (180°, 12 hr, 88% yield) to yield 429. Oxo groups in the 2- or 4-positions were... 

Only a few displacements involving mono-substituted compounds are known. 4-Chloropyrido[2,3-d]pyrimidine reacts readily (96°, 30 min) with aqueous aniline, hydrazine, or ammonia and with diethylamine (0°, 16 hr). In contrast to the 1,3,6-isomers, the 4-oxo and 2,4-dioxo derivatives are readily converted into chloro and thioxo derivatives by phosphorus oxychloride and pentasul-... 

Dioxo derivatives of 474 are known, " as well as 5-chloro-1,2-dihydro-1 -methyl-3-oxo-l,2,4,6,8-pentaazanaphthalene. ... 

Heating the 8-amino-7-chloro-2-oxo-l,2,4-triazolo[l,5-c]pyrimidine 189 with hydrochloric acid caused hydrolysis of the chloro group yielding the 2,7-dioxo derivative 190 (68JOC530) (Scheme 72). 

Linearly annelated 2-methyl-4,9-dioxo-4,9-dihydrooxazolo[4,5-g]quinoline 14 was prepared in 31% yield by cyclization of 6-acetamido-7-chloro-5,8-dioxo-5,8-dihydroquinoline in acetic anhydride and sulfuric acid (59LA108). 

The isomeric 2-substituted 4,9-dioxo-4,9-dihydrooxazolo[5,4- ]quinolines 15 were prepared in the same way starting from corresponding 6-chloro derivative (91CCC1919). 

Acetylation of 6-amino-7-chloro-5,8-quinolinedione and subsequent replacement of the chlorine atom to a -SH and then a -SMe group gave the final linear 2-methyl-4,9-dioxo-4,9-dihydrothiazolo[4,5-g]quinoline 40 (59LA108). 

The isomeric thiazolo[5,4-g]quinoline skeleton was prepared from 6-chloro-quinoline-5,8-dione hydrochloride by reaction with thiourea, resulting in the 2-amino-4,9-dioxo-4,9-dihydroderivative 42 (91CCC1919). 

Chemical Name N,N -[(1,2-dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl)] bis[2-chloro-N,N-diethylbenzenemethanaminium] dichloride... 

Chemical Name 7-chloro-4-dimethylamino-1,4,4a,5,5a,6,11,12a octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11 -dioxo-2-naphthacenecarboxamide... 

Chemical Name Sodium 7-[8-chloro-10-dioxo-11-methyldibenzo[c,f] thiazepin-(1,2)-5-yl] aminoheptanoate... 

The same substrate (254) with 2,3-dichloromalonic anhydride (257) gave 6-chloro-2-(4,5-dichloro-3,6-dioxo-1,2,3,6-tetrahydropyridazin-l-yl)quinoxa-line (258) (AcOH, reflux, 3 h 87% analogs likewise). 

V-[[l-[4-chloro-2-(2-chlorobenzoyl)phenyl]-3-[(dimethyl-amino)carbonyl]-l/f-l,2,4-triazol-5-yl]methyl]-l,3-dihy-dro-l,3-dioxo-2H-isoindole-2-acetamide (C29H22CI2NSO5 65699-00-5) see Rilmazafone... 

C H24C1FN20 32566-12-4) see Flurazepam 4 -chloro-fV-[2-(diethyIamino)ethyl]-a-(o-ffluorophenyl)-W hydroxy-13-dioxo-2-isoindolineaceto-o-toluidide (C29H29CIFN3O4 32566-13-5) see Flurazepam... 

Isopropylcatechol, see Isopropylbenzene Isopropyl-l-chloro-2,3-dioxo-l-indanecarboxylate, see... 

Demeclocycline Demeclocycline, 7-chloro-4-dimethylamino-l, 4,4a,5,5a,6,11,12a-octahy-dro-3,6,10,12,12a-pentahdroxy-l,ll-dioxo-2-napthacencarboxamide (32.3.4), is prodnced by a mntant strain of S. aureofaciens, in which the mechanism of transferring methyl gronps is disrapted, and thus demeclocycline or demethylchlorotetracycline differs from chlorotetracycline, oxytetracycline, and tetracycline in the absence of a methyl gronp at Cg of the hydronaphthacene system. As a result, an antibiotic is synthesized that is more resistant to acids and bases in comparison with the methyl homologs [215-221]. 

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