Quinolines 1,2,3,4-tetrahydro- from

IH-chromene synthesis from, 3, 766 Quinoline, 4-acetoxy-1,2,3,4-tetrahydro-synthesis... 

Quinolin-2-one, 5,6,7,8-tetrahydro-synthesis, 2, 404 from cyanoacetamide, 2, 460 Quinoin-4-one, 1-alkyl-antibacterial activity, 1, 180 Quinolin-4-one, 2-amino-synthesis... 

When 3-phenyl-3//-triazolo[4,5-/]quinoline was heated at 390 00°C, IH-pyrido[2,3-c]carbazole 149 originated. Its structure could be confirmed by unambiguous synthesis from the 8,9,10,1 l-tetrahydro-7//-pyrido[2,3-c]carbazole (52CJC711). 

The Reisert compound 93, prepared from quinoline derivatives 92, gave upon reaction with dimethyl acetylenedicarboxylate the pyrroloquinoline 95. Reduction of 93 gave the tetrahydro derivative that upon reaction with dimethyl acetylenedicarboxylate afforded 96 (85JOC722). Reaction of 94 with acrylonitrile in presence of base gave pyrroloquinoline 97 (77JCS(P1)2018) (Scheme 18). 

A solution of N-(2-aminobenzvl)-1-phenyl-2-metKylaminoethanol-1 was prepared by the reaction of a-bromo-acetophenone and (2-nitrobenzyl)methylamine, followed by hydrogenation of the nitro group by means of nickei on diatomaceous earth at room temperature and reduction of the CO group by means of sodium borohydride. The intermediate thus produced was dissolved in 100 ml of methylene chloride and introduced dropwise into 125 ml of sulfuric acid at 10° to 15°C. After a short standing, the reaction mixture was poured onto ice and rendered alkaline by means of a sodium hydroxide solution. Dy extraction with ether, there was obtained 1,2,3,4-tetrahydro-2-methyl-4-phenyl-8-amino-iso-quinoline. The base is reacted with maleic acid to give the maleate melting point of the maleate 199° to 201°C (from ethanol). 

Nitropyrido[l,2-A]quinolin-6-ium-l 1-olate (6%) was isolated from a reaction mixture obtained by photoirradiation of crystalline photochromic 2-(2, 4 -dinitrobenzyl)pyridine for 10 days <2004JP0865>. Reaction of l-(3-chloropropyl)-6,7-dimethoxy-3-methylbenzo[c]pyrylium perchlorate with hydrazines and hydroxylamine in refluxing MeOH afforded 9,10-dimethoxy-6-methyl-, -4,6-dimethyl-l,2,3,4-tetrahydropyridazino[6,l-tf]isoquinoli-nium, and 9,10-dimethoxy-6-methyl-l,2,3,4-tetrahydro[l,2]oxazino[3,2- ]isoquinolinium, perchlorates, respectively <2004CHE1131>. 

Nitrogen heterocycles undergo C-allylation in the presence of metalacyclic iridium-phosphoramidite catalysts. Recently, Yu and coworkers reported the C-allylation of indoles with the iridium catalyst derived from LI [86] and from phosphoramidites containing 2-methylindoline- and 2-methyl-l,2,3,4-tetrahydro-quinoline as the amino group (Table 4) [87]. No N-allylation was reported. However,... 

Among the simplest syntheses of this type are those of tetrahydro-quinolines or -iso-quinolines based on Friedel-Crafts cyclizations. The use of side-chain halides is shown by the synthesis of 1,2,3,4-tetrahydroisoquinolines (158) (71CC799), and of 3,4-dihydroquinol-2-ones (159) (27CB858). Electrophilic carbon atoms can be developed from secondary or tertiary alcohols, or from alkenes or alkynes. In the synthesis of the tetrahydroisoquinoline... 

Imines derived from aniline and glyoxylic acid esters can be regarded as electron-poor 2-azadienes, in which an aromatic carbon—carbon double bond takes part of the diene system. In this context, Prato and Scorrano et al. were able to achieve the [4 + 2] cycloaddition of ethyl N-phenyl glyoxylate imines with dihydrofuran and indene leading to hexahydrof-uro[3,2-c]- and tetrahydro-7//-indeno[2,l-c]quinolines, respectively, in moderate to good yields (88JHC1831). Similarly, tetrahydroquinoline derivatives were formed by [4 + 2] cycloaddition of 1,2-bis(trimethylsily-... 

Sodio malononitrile, prepared from malononitrile with 57% sodium hydride in dimethylacetamide, and l-(3-chloropropyl)isatoic anhydride (398) at room temperature for 30 min, then at 120°C for 18 h, gave 6-oxo-l,2,3,4-tetrahydro-6//-pyrimido [1,2-a quinoline-5 -nitrile (399) (76JOC825). 

Reaction of piperidine-2-thione and diphenylcyclopropenone in acetonitrile gave 2,3-diphenyl-2,3,4,6,7,8-hexahydropyrido[2,l-b][l,3]thiazin-4-one in 88% yield [71LA(752)136], 2,6,7,llb-Tetrahydro[l,3]thiazino[2,3-a]iso-quinolines (214) were obtained from 1-substituted 3,4-dihydroisoquino-... 

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