Pyrido quinazolin-4-ones

The lipophilicity (7 m value) and specific hydrophobic surface area of 1 ]/f-pyrido[2,]-fi]quinazolin-] 1-one and its isomeric 6//-pyrido[l, 2-u]qui-nazolin-6-one were determined by reversed-phase thin-layer chromatography (98MI4). 

Bond orders, charges on the atoms in 1 l//-pyrido[2,l-Z)]quinazolin-l 1-one and its protonated form were calculated by quantum chemical calculations by the semiempirical AMI method. According to the results, the equilibrium conformation of the ring in 1 l//-pyrido[2,l-Z)]quinazolin-l 1-one is planar, while l//-pyrimido[l,2-u]quinolin-1-one adopts a conformation close to a half-chair due to the unfavorable interactions between the oxygen atom of the carbonyl group and the ring C-10 atom in the pen-position (97MI22). 

Ozonolysis of 6-(phenylmethylene)-6,7,8,9-tetrahydro-l l//-pyrido[2,l-fi]-quinazolin-11-one in CH2CI2 gave 6,7,8,9-tetrahydro-l l//-pyrido[2,l-fi]-quinazoline-6,11-dione (01H(55)1555). 

Condensation of 6,7,8,9-tetrahydro-l]/f-pyrido[2,]-6]quinazolin-ll-one and PhCHO in boiling AC2O for 48 h yielded a 6-phenylmethylene derivative (01H(55)1555). 

Cyclization of 2-(4-hydroxypentyl)quinazolin-4(3//)-ones 422 under Mitsunobu s conditions afforded only linearly fused 6,7,8,9-tetrahydro-1 l/f-pyrido[2,l-6]quinazolin-l l-ones 423 without angularly fused 1,2,3,4-tetrahydro-6//-pyrido[l, 2-n]quinazolin-6-ones 424 (98CPB928). 

Oxidative cyclization of 1 -[(2 -aminocarbonyl)phenyl]piperidine and its 4 -substituted derivatives with Hg(OAc)2-EDTA reagent afforded 1,2,3,4-tet-rahydro-6//-pyrido[2,l-Z)]quinazolin-6-one and its 3-substituted derivatives in 36-82% yields (99ZN(B)1577). Similarly, ( )-2-(piperidin-2-yl)benzal-doximes gave 2,3,4,4u-tetrahydro-l//-pyrido[l,2-u]quinazolin-5-oxide and... 

Reaction of 2-aminopyridine and 2,3,4,5,6-pentafluoro- and 5-nitro-2-fluorobenzoyl chloride in CH2CI2 in the presence of (/-Pr)2EtN at room temperature afforded 1,2,3,4-tetrafluoro- and 8-nitro-l l//-pyrido[2,l-6]-quinazolin-11-ones, respectively (01TL1851). 

The reaction of methyl anthranilate and 3-amino-2-chloropyridine in 1,2,4-trichlorobenzene in the presence of KOt-Bu at 50 °C gave 5,1 l-dihydro-6//-pyrido[2,3-Z)]benzodiazepin-6-one and 6-amino-ll//-pyr-ido[2,l-Z)]quinazolin-l 1-one as a by-product (99BMCL3031). 

Reaction of 1 -methylene-1,2,3,4-tetrahydro-5//-pyrazino[2,1 -Z)]quina-zoline-3,6-diones (435) with PhLi and MeMgBr in THE at —78°C gave a mixture of 1 l//-pyrido[2,l-Z)]-quinazolin-l 1-ones 435-439 (01T1987). 

The use of 1 l//-pyrido[2,l-Z)]quinazolin-l 1-ones in an organic electroluminescent device was patented (99JAP(K)99/74080). 2//-Pyrimido[2,l-n]isoquinolin-7-ols were patented as multi-functional fuel and lube additives (97USP5646098). 

Phenyl-5,6-dihydro-l//,7//-pyrido[3,2,l-//]quinazoline-7-one and 1,7-dione 179 (X = H2 and O) were prepared from tetrahydroquinolines 206 and 207 with A-(ethoxycarbonyl)thiobenzamide and PhCOCl, respectively (98EJM763). 

Tetracyelie derivatives 215 formed exclusively from imines 213 on the action of TMSOTf, whereas in the presence of TiCl4 both l//-pyrido[l,2-c]quinazolin-6-ones 214, as a >9 1 mixture of a//3 ehloro epimers, and tetraeyelie derivatives 215 were obtained. Imine 213 (R = H) gave a 3 1... 

Treatment of l,3,4,6,7,llb-hexahydro[l,3]oxazino[3,4- ]quinazolin-l-one with LAH in boiling THF gave 2-(2-hydroxyethyl)-l-methylquinoline <2003T6785>. Pyrimidinone 107 was obtained from trequinsin 106 on the action of NaH, followed by the treatment with Mel (Equation 17) <1997IJB349>. The reaction of7-(benzotriazol-l-yl)-6,7-dihydro-l//,3/7,5//-pyrido[3,2,l-zy][3,l ]bcnzoxazine with PhMgBr led to ring-opened l-benzyl-4-(benzotriazol-l-yl)-8-hydroxymethyl-l, 2,3,4-tetrahydroquinoline < 1995JOC3993>. 

Enantiomers of racemic hyperaspine 93 could be separated on a Chiralcel column by means of HPLC <2005EJ01378>. Enantiomers of racemic 7-amino-3-(4-mcthoxyphenyl)-2,3,6,7-tetrahydro-l//,5//-pyrido 3,2,l -//]-quinazolin-l-one were separated on a Chiralcel column by means of HPLC <2006USA0004028>. 

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