Pyrimido quinoline

In the pyrimido[4,5-c]quinoline series the 1-chloro derivative (104) reacts with a variety of nucleophiles (57JCS3718), as does a 2-chloro in (105) in the isomeric pyrimido[5,4-c]quinoline series (66MI21S00). 

Other syntheses involve preformed quinoline systems in standard syntheses, including examples in the pyrimido[4,5-fe]quinoline (e.g. 200 201) (71JHC111>, pyrimido[4,5-clquinoline (e.g. 202 203) (62JCS1671) and pyrimido[5,4-c]quinoline (e.g. 204 205) (78JMC295> series. 

Additional pyrimido[4,5-f ]quinoline syntheses include one involving the action of cyanogen bromide on 2-chloro-3-cyanoquinoline similar to that described for pyridines (Section 2.15.5.5.1) (78JHC877), and a synthesis of pyrimido[4,5-fe]quinoline-2-carboxylic... 

Reactions of 6-aminouracils with various 2-substituted cyclohexanones such as the aldehyde (264) give reduced pyrimido[4,5-f ]quinolines (265) (57BRP774095, 58JA3449), and other cyclohexanone derivatives used include the 2-dimethylaminomethyl (Mannich) bases (78AP542) and the 5-benzylidenedimedones (266) formed in situ from dimedone and aldehydes (67KGS395, cf. 67KGS406). 

In the case of the 2-dimethylamino- (or 2-amino-)methylene derivatives, the products were at first thought to be pyrimido[4,5-c]isoquinolines (267), but later work with 6-(N-substituted amino)uracils assigned the structures of the products (268) as belonging to the isomeric pyrimido[4,5-f>]quinoline system (74CB2537), in agreement with the regioselection rules above. 

PyrimidoX4,5-6]quinoline-2-carboxylic acids synthesis, 3, 224-225 Pyrimido[4,5-6]quinoline-2,4-diones synthesis, 3, 224 Pyrimido[5,4-6]quinolinediones synthesis, 3, 219 Pyrimido[4,5-6]quinolines synthesis, 3, 219, 224, 227, 228, 230, 231 Pyrimido[4,5-c]quinolines synthesis, 3, 224, 227 tautomerism, 3, 205 Pyrimido[5,4-6]quinolines synthesis, 3, 227 Pyrimido[5,4-c]quinolines synthesis, 3, 219, 224, 227, 230 Pyrimido[5,4-6]quinoline-1,3,5-trione, 7-chloro-synthesis, 3, 221... 

Pyrimido[4,5-6]quinolinium salts pseudo bases - ring opening, 3, 208 Pyrimido[4,5-6]quinolinium salts, 4-chloro-hydrolysis, 3, 214 Pyrimido[4,5-6]quinolinones synthesis, 3, 228 Pyrimido[4,5 -6]quinolin-5-ones synthesis, 3, 221-222 Pyrimidothiadi azoles reactions, 6, 533 Pyrimidothiazines synthesis, 4, 527 Pyrimidothiazinones mass spectra, 2, 23... 

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 5,8,9-trihydroxy-2,3-dihydro-l//-pyrimido[l, 2-n]quinoline-3-carboxylic acid (420), obtained from isopyoverdin isolated from Pseudomonas putida BTPl by acidic hydrolysis, gave l-2,4-diaminobutyric acid, which confirmed the hypothesis that heterocyclic chromophores 1 and 4 of pyoverdin and isopyoverdin, respectively, could have the same precursor, and the configuration at C(3) should be 5 (97ZN(C)549). 

Methyl-l//-pyrimido[l,2-a]quinolin-l-one was obtained by heating isopropylidene 2-[l-(2-quinolylamino)ethylidene]malonate in EtOH at 20 °C (00MI40). 

Cyclocondenzation of 2-aminoquinoline and isopropylidene 2-(l-methylthioalkylidene)malonates on Si02 under microwave irradiations afforded 3-substituted (3-methylthio, 3-methyl, 3-ethyl, and 3-phenyl) l//-pyrimido[l, 2-n]quinolin-1-ones (00MI40). 

Trihydroxy-2,3-dihydro-l//-pyrimido[l,2-u]quinoline-3-car-boxylic acid and (420) and its (15)-1-carboxylic acid isomer were isolated from isopyoverdins (97ZN(C)549, 01T1019) and pyoverdins (99MI27), respectively, after acidic hydrolysis in 3 M HCl for 5 days at 110°C. 

ZN(C)153, 00ZN(C)323, 00ZN(C)857, 01MI2, 01MIP4, 01TL5849). 5-Amino-8,9-dihydroxy-2,3-dihydro-l//-pyrimido[l,2-u]quinoline-3-carboxylic acid moiety 4 was also identified as a chromophoric moiety of certain... 

Dimethoxy-2-(arylimino)-2,3,6,7-tetrahydro-4//-pyrimido[6,1 -n]iso-quinolin-4-ones were N-alkylated with A-(catalytic amount of I2 in boiling 2-butanone in 13-67% yields (00MIP19). 

Cyclocondensation of a-aryl-2-pyridylacetamides and 2-(3,4-dihydroiso-quinolin-l-yl)acetamide with Et2C03 in the presence of NaOEt in boiling EtOH afforded 4-aryl-2,3-dihydro-l//-pyrido[l,2-c]pyrimidine-l,3-diones (99JHC389) and 6,7-dihydro-4//-pyrimido[6,1 -a]isoquinoline-2,4-dione (98MIP15), respectively. 

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