Pyrido quinoline derivatives

Methyl 2-benzoylamino-3-dimethylaminopropenoate afforded with methyl 2-quinolylacetate a pyrido[l,2-a]quinoline derivative 133 (94JHC125). 

A search of the literature from 2006-7 reveals a large number of reports regarding the biological activities of this type of system, for example the synthesis and antiproliferative evaluation of certain pyrido[3,2-g]quinoline derivatives has been reported <2006BMC7370>. 

Interaction of substituted dienediamines with ethylenediamine yields im-idazo[3,2-n]pyridine derivatives (95JHC477). 3-Arylaminoindoles, with distinct enamine properties, are the starting materials for the synthesis of indolo[3,2-b]quinoline derivatives [96KFZ(7)42]. a-Carboline derivatives can be obtained from enamine-based 3-dimethylamino-2-indolinones [96KFZ(9)35, 96KFZ(10)32], The synthesis and transformation of enamines based on the pyrido[l,2-n]pyrazine ring system into imidazo[l,2-n]pyridine and imidazo[l,2-a]pyrimidine derivatives have been reported... 

The pyrido[l,2-a]pyrimidines (256) undergo an essentially similar ring transformation, with the difference being that the ring closure of the intermediate iminoketene (257) takes place not to the C-3 atom of the pyridine ring but to the more reactive phenyl ring, and thus a quinoline derivative (258) is isolated.327... 

The pyrido[2,3-/ ]pyrazines, 185-187, have been identified in the defensive secretion of the giant springtail, Tetrodontophora hidanensisP The secretion appears to confuse and strongly disorient potential predators. An unusual quinoline-derived betaine (188) with defensive properties was recently identified from the blood of Photuris versicolor fireflies. In addition, these fireflies chemical defense relies on sequestered cardiotonic steroids, the lucibufagins (see Section 2.04.3.3) (Figure 44). ... 

Microwave-assisted solvent-free synthesis of pharmacologically important pyrido fused-ring systems has recently been accomplished and is an improved method for assembly of a variety of pyridopyridazine and quinoline derivatives. Benz-1,3-oxazine formation has also been investigated in dry media using AI2O3-KF as a solid base (Scheme 8.75) [187]. 

Treatment of N-2,4-dinitrophenylpyridinium chloride (778) with phenyl-hydrazine in acetic acid causes reductive cyclization to yield the pyrido[l,2-ajimidazole (779). 3-Aminocrotononitrile, MeC(NH2)=CHCN, condenses with quinoline 1-oxide and isoquinoline 2-oxide to form the tricyclic compounds (780) and (781), respectively." The imidazo[5,l-a]isoquinoline derivative (783) is obtained by the action of phenyl isothiocyanate on the sodium salt of the Reissert compound (782)." ° Triethyl phosphite reduces the o-nitrophenyldipyr-rolylmethane (784 R=N02) to the nitrene (784 R = N), which forms the pyrrolo[3,2-6]quinoline derivative (785) by an intramolecular insertion reac-tion." 3-Amino-177-isoindole (786) reacts with acetylacetone in the presence of perchloric acid to yield the pyrimidoisoindolium salt (787). ... 

Abdolmohammadi S (2013) Simple route to indeno[l,2-6]quinoline derivatives via a coupling reaction catalyzed by TiO nanoparticles. Chinese Chem Lett 24 318—320 Symeonidis TS, Lykakis IN, Litinas KE (2013) Synthesis of quinolines and fused pyrido-coumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO. Tetrahedron 69 4612 616... 

The UV spectra of pyrido[2,3-d]pyridazine-l,4-diones have been recorded (68MI21501), whilst several of the latter were also used in chemiluminescence studies. Quinolinic and cinchomeronic hydrazides showed no chemiluminescence (60NKK173, 37JPR(148)135), but it was observed in the 8-hydroxy derivative (305) (72YZ703). 

Reactions involving quinoline hydrazide derivatives have been noted in the pyridazino-[4,3-c]- (64MI21500), -[4,5-f ]- (31M(58)238) and -[4,5-c]-quinoline (71CB3341) series, whilst the double cyclization of (358) to the pyridazino[4,5-f ]quinoline (359) (80CPB3457) and related cyclizations in the same series (80H(14)267) are of a basically similar type. A lone cyclization of this type from cinnoline intermediates involves the o-acetonylcarboxamide type formation of the pyridine ring to give the pyrido[3,4-c]cinnoline (360) (76JCS(Pl)592). 

Perhydro derivatives of pyrido[l,2-7)][l,2]oxazines are frequently applied in the total synthesis of various alkaloids to control the stereochemistry, and pyrido[l,2-c][l,3]oxazines and [l,3]oxazino[3,4-u]quinolines were also used in the stereoselective syntheses of different alkaloids. Perhydropyrido[l,2-c][l,3]oxazines and their benzologs are formed form 2-(2-hydroxyethyl) piperidines and from their benzologs to justify the stereochemistry of 2-(2-hydroxyethyl) derivatives. Different optically active pipecolic acids can be prepared via 4-phenylperhydropyrido[2,l-c][l,4]oxazin-l-ones. 

Reaction of 2,3-dihydro-3-hydroxy-3-methyl- 240 (R = Me), or a mixture of 2,3-dihydro-3-hydroxy-3-aryl-57/-pyrido[l,2,3-dfe]-l,4-benzoxazin-5-ones 240 (R = Ar) and (8-aroylmethoxy)quinolin-2(l//)-ones 241 (R = Ar) with ethyl 2-(bromomethyl)acrylate in the presence of activated Zn and hydroquinone gave 8-[(2,3,4,5-tetrahydro-4-methylidene-5-oxo-2-furanyl)-methoxy]quinolin-2(l//)-ones (242) (97HCA1161). 6,7-Dihydro derivatives of 240 reacted similarly (00HCA349). 

Synthesis of the ortho- and peri-fused pyrido[3,2,l- 1[l,3,2]benzodiazaphosphorine ring system was accomplished from the quinoline carboxamide derivative 197 by treatment with phosphoryl chloride <1978JHC1169, 1979JHC897>. The iV-chloropropyl derivative 198b could be transformed to the tetracycle 199 (Scheme 27) <1979JHC897>. 

Pyrido[l,2,3- ][l,4,2]benzoxazasilin-4-ium chloride 208, the benzo derivative of pyrido[l,2-rf][l,4,2]oxazasiline ring system, was synthesized starting from the quinoline precursor. Thus, reacting compound 206 with chloromethyl-dimethylsilyl chloride afforded the tricycle 208 via the intermediate 207, but no yields were reported (Scheme 31) <1996ZOB1949>. 

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