Facile synthesis of 2-[1-(alkylthio)alkyl]pyridines and phenyl-substituted derivatives

The title compounds 5 are produced in the reaction of N-fluoropyridinium tetrafluoroborate ( 1 ) with sulfides 2 . The proposed mechanism involves single-electron transfer from 2 to 1 followed by transformations of the resultant radical intermediates.     

Synthesis and microbial screening of 8-(benzyloxy)-5-(2-[1,3-diphenyl-1H-pyrazol-4-yl]thiazol-4-yl)quinolin-2(1H)-one derivatives

The present investigation describe the synthesis of 8-(benzyloxy)-5-(2-[1,3-diphenyl-1H-pyrazol-4-yl]thiazol-4-yl)quinolin-2(1H)-one derivatives. Quinolin-8-ol was transformed by five step synthetic procedures into 8-Benzyloxy-5-(2-bromo-acetyl)-1H-quinolin-2-one. Subsequently, 8-Benzyloxy-5-(2-bromo-acetyl)-1H-quinolin-2-one condensed with 1,3-Diphenyl-1H-pyrazole-4-carbothioic acid amide in the presence of acetonitrile to afford 8-(benzyloxy)-5-(2-[1,3-diphenyl-1H-pyrazol-4-yl]thiazol-4-yl)quinolin-2(1H)-one derivatives. Synthesized compounds were screened for their antimicrobial activity against gram-positive and gram-negative bacteria. Most of the synthesized compounds are found to be active against tested bacterial strains and fungal strain.     

“一锅法”合成11,11′-双(8,11-二氢苯并[f]呋喃并[3,4-b]喹啉-10-酮)(英文)

微波辐射下,不使用催化剂,在醋酸和DMF的混合溶剂中二醛、季酮酸和萘胺反应,"一锅法"合成11,11′-双(8,11-二氢苯并[f]呋喃并[3,4-b]喹啉-10-酮)。所合成化合物的结构经红外光谱、核磁共振光谱和高分辨率质谱予以确证。该方法具有产率高、操作简单、反应时间短等优点。     

Derivatives of arborine [1-methyl-2-(phenylmethyl)-4(1H)-quinazolinone]

A method has been developed for the reaction of 2-cyanomethylbenzoic acid with N-methylanthranilic acid to give 2-[(1-methyl-4-oxo-1,4-dihydro-2-quinazolin-2-yl)methyl]benzoic acid, its esters were synthesized. The spectroscopic chracteristics of the isomeric compounds have been studied and compared in solution and in the solid state. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1532–1538, October, 2007.     

Green synthesis of naphtho[2,3-f]quinolin-13-one and naphtho[2,3-a]acridin-1(2H)-one derivatives catalyzed by heteropoly acid supported montmorillonite K-10 clay

Herein, synthesis of a series of naphtho[2,3-f]quinolin-13-one and naphtho[2,3-a]acridin-1(2H)-one derivatives directly by one-pot multi-component reaction of 1,3-dicarbonyl compounds (1,3-indanedione/1,3-cyclohexanedione), 2-aminoantharacene/2-naphthylamine and various substituted aldehydes under solvent-free conditions using heteropoly-11-molybdo-1-vanadophosphoric acid supported on montmorillonite K-10 clay catalyst (10% PVMoK-10) is reported. The successful formation of naphtho[2,3-f]quinolin-13-one and naphtho[2,3-a]acridin-1(2H)-one derivatives was confirmed by various spectroscopic techniques. This study offers a green approach for the synthesis of novel quinolinone derivatives.     

Kinetic study on the synthesis of some benzo[g]quinoxalin-2(1H)-one derivatives

Some novel 3-substituted benzoquinoxalinones [R = H, CH₃, C₆H₅, (CH₂)₂COOH] were synthesized by the Hinsberg reaction between 2,3-diaminonaphthalene and several α-dicarbonyl compounds. The course of the reactions was followed by the second uv/visible Derivative Spectroscopy Method at different pH values (-0.89 to 9.0) and also in organic solvents at 25°. The compound non-substituted at C-3 was the only one that could be obtained in every media in good yields (80%), having pseudo first-order anelation rate constants of relative high values (1 × 10^?1 — 1 × 10^?2 min^?1). On the other hand, only methanol could be used as the organic solvent for the synthesis of all of the other compounds; aqueous media always provided better results. In the 3-methyl derivative, as well as in the 3-phenyl derivative the change of the reaction pH medium modified the stoichiometry of the anelation, turning a non-quantitative reaction into a quantitative one. This is explained by a change in the mechanism of the reaction on going to lower hydrogen concentrations, a fact that was supported by complementary quantitative hptlc experiments. In general, pseudo first-order rate constants for the anelation were one or two logarithmic units lower than those of the non-substituted compound (R_C-3 = H), but yields were above 60% in every case. A reaction scheme is presented which includes a probable mechanism.     

Synthesis of imidazo[4,5-c]quinolin-4(5H)-one via radical cyclization

The tributyltin radical-induced cyclization of N-(2-bromophenyl)-Nbutyl-1H-1-methylimidazole-4-carbox-amide 3 gave 5-butyl-3-methyl-3H-imidazo[4,5-c]quinolin-4(5H)-one 5 via [1,2]-acyl rearrangement.     

Synthesis and Crystal Structure of 4-（4-Bromophenyl）- 3,4-dihydro-6-methyl quinolin-2（1H）-one

The title compound (C16H14BrNO) has been synthesized by the reaction of p-tolylamine, Meldrum’s acid and 4-bromo-benzaldehyde, and its structure was characterized by IR, 1H NMR and X-ray single-crystal diffraction. The crystal belongs to monoclinic, space group P21/n with a = 7.6850(11), b = 8.3004(11), c = 21.301(3) , β = 95.110(2)°, V = 1353.4(3) 3, Mr = 316.19, Z = 4, Dc = 1.552 g/cm3, μ(MoKα) = 3.028 mm-1, F(000) = 640, the final R = 0.0345 and wR = 0.0768. X-ray analysis reveals that the atoms of C(1), C(2), C(3), C(4), C(5) and N(1) form a six-membered ring of boat conformation.     

Catalyst-free three-component approach to efficient synthesis of chromeno[4,3-b]pyrrol-4(1H)-one derivatives

A mild, efficient, and environmentally benign one-pot synthesis of functionalized chromeno[4,3-b]pyrrol-4(1H)-ones by a three-component domino reaction of 4-aminocoumarins, arylglyoxal monohydrates, and 1,3-dicarbonyl compounds in refluxing ethanol without the use of catalyst is reported. The present protocol features operational simplicity, short reaction time, good yields, and the absence of aqueous workup procedure and chromatographic separation.