Microwave-assisted synthesis of quinoline alkaloids: 4-Methoxy-1-methyl-2-quinolinone and its analogs

Abstract

The microwave-induced synthesis of some quinoline alkaloids of the type 4-methoxy-1-methyl-2-quinolinone including folimine is reported. The precursors 4-hydroxy-2-quinolinone derivatives were effectively prepared in a single step from aniline and diethylmalonate using ptoluenesulfonic acid as a catalyst and these intermediates were converted to the titled quinoline alkaloids by treatment with dimethyl sulfate, N,N-dimethylformamide and potassium carbonate. The presented synthentic procedure is a convenient, simple and fast alternative for synthesizing 4-methoxy-1-methyl-2-quinolinone and its derivatives.

One-Pot Three Component Domino Reaction for the Synthesis of Novel Isoxazolo[2,3-<i>c</i>][1,3,5]Thiadiazepin-2-Ones Catalyzed by <i>PTSA</i>—A Green Chemistry Approach

“…Isoxazolo[2,3-c][1,3,5]thiadiazepin-2-ones 4 exhibited characteristic absorption bands at 1680 and 1620 cm −1 due to C=O and C=N functional group stretching vibrations respectively. 1 H NMR spectra of 4 displayed to prominent singlets at δ 4.27 and 5.50 due to CH 2 and NCHAr proton respectively confirming the cyclization 13. C NMR spectra of 4 is consistent with the proposed structure by displaying the absorption peaks at 39.57, 66.05, 160.32 and 193.47 due to CH 2 , NCHAr, C=N and C=O carbons respectively.…”

“…1 H NMR spectra were recorded on a Varian Gemini 300 MHz spectrometer. 13 C NMR spectra were recorded on a Bruker 75 MHz spectrometer. Chemical shift values are given in ppm (δ) with tetramethyl silane as internal standard.…”

“…][1,3,5] thiadiazepin-2-ones. The structure of the products 4a-j have been established on the basis of spectral (IR, 1 H NMR,13 C NMR and MS) and analytical data. Isoxazolo[2,3-c][1,3,5]thiadiazepin-2-ones 4 exhibited characteristic absorption bands at 1680 and 1620 cm −1 due to C=O and C=N functional group stretching vibrations respectively.…”

Synthesis and biological evaluation of some hybrid 2-quinolinone derivatives containing cinnamic acid as anti-breast cancer drugs

“…Kemnitzer et al [13] found a new series of apoptosis inducers, the 1-benzoyl-3cyanopyrrolo [1,2-a]quinolines (Formula I), among which the compound 1-(4-(1H-imidazol-1yl)benzoyl)-3-cyanopyrrolo[1,2-a]quinolone (Formula II) displayed high cytotoxic activity in T47D human breast cancer, HCT-116 human colon cancer cells and SNU398 hepatocellular carcinoma cells. 2-quinolone derivatives have been shown to have antitumor, antimalarial, antiviral, antioxidant, antidepressant, cardiac stimulant, and anti-asthmatic biological activity [14][15][16][17][18][19][20][21][22][23][24]. Quinoline is a scaffold with pharmacological value spread in a variety of synthetic and natural compounds that are bioactive [25].…”

Efficient Synthesis of 4-Hydroxybenzo[h]Quinoline-2(1H)-One and Some Derivatives

“…Recently we have synthesised a series of hydroxyl-quinolone derivatives and used them as precursors to prepare some novel azo disperse dyes. [13][14][15] As a part of our ongoing efforts towards the synthesis of 4-hydroxyquinolin-2(1H)-one derivatives, 16,17 we have synthesised 4-hydroxybenzo[h]quinolin-2-(1H)-one (Scheme 1) and prepared some new 4-hydroxyquinolin-2(1H)-one derivatives (Scheme 2).…”