Quinazoline-4-carboxylic acids

Quinazoline-2-carboxylic acids and quinazoline-4-carboxylic acids ... 

A pyrimido[ 1,2-c]quinazoline-4-carboxylic acid derivative (FR50948) exhibits excellent antiallergic effects <88MI 825-01 >. 

Quinazoline-4-carboxylic acids from isatinic acids... 

Condensation of the substituted quinazoline carboxylic acid (215) with the polyglutamyl derivative (216) using DEPC as coupling agent provides quinazoline antifolates (217).81... 

Elimination of lorazepam occurs by metabolism within the hver and renal excretion of the metabolites. Glucuronidation to form lorazepam-glucuronide is the major pathway for metabolism. Minor metabolites include a hydroxylated derivative, a quinazolinone derivative and a quinazoline carboxylic acid. Seventy... 

The recorded use of metallo derivatives in the pyrimidine and quinazoline series is minimal. The best described pyrimidinyllithium compounds are those derived from 5-bromopyrimidines. Their reactions are illustrated in the following examples. Pyrimidin-5-yllithium (474 R = H) reacts with solid carbon dioxide under ether to give pyrimidine-5-carboxylic acid (475 R = H) in good yield (65ACS1741) 4,6-dimethoxy- (474 R = OMe),... 

The structures of 5-ethyl-1 ]-methyl-9-oxo-5,l l-dihydro-9/7-pyrido[2,1-6]-quinazohne-8-carboxylic acid (00K669), the chromophore 4 of isopyoverdin siderophores (01T1019), and that of 5,5n,6,7,8,9-hexahydro-l l//-pyrido [2,]-6]quinazoline (99SL1383) were justified by X-ray analysis. 

A-Substituted 11-oxo-l l//-pyrido[2,l-6]quinazoline-6-carboxamides were prepared from 11-oxo-l l//-pyrido[2,l-6]quinazoline-6-carboxylic acids and amines in the presence of (/-Pr)2EtN and benzotriazol-l-yloxytris(dimethy-lamino)phosphonium hexafluorophosphate in CH2CI2 (98MIP1, 98MIP2, 99USP5908840, 99USP5914327). 

Heating 6-[(2-carboxylphenyl)amino]-5-cyano-2-methylpyridine-3-carboxylate in refluxing POCI3 afforded 6-cyano-8-ethoxycarbonyl-9-methyl-ll//-pyrido[2,T3]quinazolin-ll-one, but in PPA at 135-145°C 2-methyl-3-ethoxycarbonyl-4-methyl-5-oxo-5,10-dihydrobenzo(3)-l,8-napthyridine-9-carboxylic acid formed <2004CHE510>. 

Cyclocondensation of 2-chloronicotinic acid with 2-amino-5-iodobenzoic acid and methyl 2-amino l-bromobenzoate in boiling EtOH in the presence of cone. HC1 gave the 2-iodo and 3-bromo derivatives of ll-oxo-117/-pyrido[2,l-A]-quinazoline-6-carboxylic acid <1998WO98/023616, 1998WO98/023617, 1999USP5908840, 1999USP5914327>. 

In total, 185 substances were found in the wing-sac liquid of male S. bilineata from a Costa Rican population. For a more detailed analysis the relative peak area of thirteen focus compounds was compared (Table 14.1). Of these nine were male-specific substances (indole, indol-3-carboxaldehyde, indole-3-carboxylic acid, 2-aminoacetophenon, anthranilic acid, SHJOH-dipyrrolofl -aT -dJpyrazine-5,10-dione (pyrocoll), indolo[2,l-b]quinazoline-6,12-dione (tryptanthrin), 2,6,10-trimethyl-3-oxo-6,10-dodecadienolide, and a compound C15H24O2 of unknown structure), three were fatty acids (tetradecanoic acid, hexadecanoic acid, and octadecanoic acid), and one a steroid (cholesterol). On average, the cumulative peak area of these substances made up 62.5 20.7% of the whole chromatogram area. 

Hu et al. (91MI1) report the Dimroth rearrangement of 2-hydrazino- to 2,3-diamino quinazolin-4-ones under catalysis of carboxylic acid derivatives this reaction is followed by an in situ cyclization in which the same carboxylic acid derivatives serve as C,-synthons. l-Acylamino-2-alkylthiopyrimidines are hydrazinolyzed and cyclized to 3-amino-1,2,4-triazolofl, 5-a]pyrimidinium salts (89EGP270711). 

The solid-state structure of (lS)-5,8,9-trihydroxy-2,3-dihydro-l/7-pyrimido-[l,2-a]quinoline-l-carboxylic acid pentahydrate was determined by X-ray investigations [91ZN(C)933. The structure of an iron(III)-containing pseudobactin, a siderophore containing a (lS)-5-amino-8,9-dihydroxy-2,3-dihydro-l//-pyrimido[l,2-a]quinazoline-l-carboxylic acid moiety (8), was determined by X-ray diffraction investigations (81 Mil). 

Oxidation of 6-formyl-5,7,8,9-tetrahydro-ll//-pyrido[2,l-b]quinazolin-11-one with potassium permanganate in pyridine at ambient temperature for 3 h gave 11 -oxo-5,7,8,9-tetrahydro-l 17/-pyrido[2,l-b]quinazoline-6-carboxylic acid in 24% yield (84JHC1301). 

Bromo-ll//-pyrido[2,l-b]quinazolin-ll-one and its 8-methyl and 8-isopropyl derivatives (127, R = Br, R1 = H, Me, iPr) were treated with carbon monoxide and nickel carbonyl in wet dimethylformamide in the presence of calcium hydroxyde to yield 2-carboxylic acid derivatives (127, R = COOH, R1 = H, Me, iPr). 2-Bromo-8-isopropyl-ll//-pyrido[2,l-b]-quinazolin-ll-one (127, R = Br, R1 = iPr) was reacted with copper(I) cyanide in iV-methyl-2-pyrrolidone at 180°C for 10 h, then with ferric chloride hexahydrate in diluted hydrochloric acid at 90°C for 30 min to give the 2-cyano derivative (127, R = CN, R1 = iPr) (85CP1189509). 

Cyclocondensation of cis- and trans-2-amino-4-cyclohexene-l-carboxylic acid with 2-methoxy-3,4,5,6-tetrahydropyrimidine in boiling chlorobenzene for 6 h gave ds-4a,lla-H- and trani-4a,lla-H-l,4,4a,6,7,8,9,lla-octahydro-1 l//-pyrido[2,l-6]quinazolin-l 1-ones (75 and 78) (90PHA109). 

Tetrazolyl)- and 2- and 8-carboxylic acids derivatives of 11//-pyrido[2,l-h]quinazolin-ll-one were patented for the treatment of hyperuricemia (88GEP3704203) and hyperlipidemia (89EUP312076) and as cardioprotective agents (90GEP3902639). 

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