Synthesis of Ethyl 2‐Amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline‐3‐carboxylates by a One‐pot, Three‐Component Reaction in the Presence of TPAB

Abstract

In this research, in order to synthesize a series of ethyl 2‐amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline‐3‐carboxylates, a green and an efficient method is proposed through one‐pot three‐component reaction of substituted arylglyoxals, ethyl cyanoacetate, and 4‐hydroxyquinolin‐2(1H)‐one in the presence of terapropylammonium bromide as a catalyst in good yields. All synthesized new substances were characterized by FTIR, 1H‐NMR, and 13C‐NMR spectral data and elemental analysis.

Aryl glyoxal: a prime synthetic equivalent for multicomponent reactions in the designing of oxygen heterocycles

“…This assembly yielded a series of ethyl 2-amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c] quinoline-3-carboxylate 85 compounds (Scheme 54). 78 Aryl glyoxal monohydrate as the same starting material was explored by Ahmad et al in 2018, with malononitrile 73 and 1,3diketones 38 in the presence of the catalyst L-proline in ethanol solvent for the facile construction of 4H-chromenes, namely 2amino-4-aroyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3carbonitrile 86 (Scheme 55). 79 M. Taheri and R. Mohebat in 2020 proposed a unique greener and environmentally friendly one-pot four-component protocol for the synthesis of pyrazolo[4 ′ ,3 ′ :5,6]pyrano[2,3-c] phenazin-15-yl)methanone 88 scaffolds in a solvent-free medium using nano Fe 3 O 4 @TiO 2 -SO 3 H as the catalyst under microwave monitoring at 75 °C.…”

“…This assembly yielded a series of ethyl 2-amino-4-benzoyl-5-oxo-5,6-dihydro-4 H -pyrano[3,2- c ]quinoline-3-carboxylate 85 compounds (Scheme 54). 78…”

“…Pyran derivatives are often screened for antianaphylatic, diuretic, spasmolytic, anticoagulant, and anticancer properties, etc. 9–11 Alkaloids possessing pyranoquinoline as the structural unit feature anti-microbial characteristics. 12 Also, a number of them act as photoactive enhancers in the treatment of neurodegenerative diseases.…”

One‐pot, three‐component synthesis of polyfunctionalized benzo[h]pyrazolo[3,4‐b][1,6]naphthyridine and benzo[g]pyrazolo[3,4‐b]quinoline derivatives in the presence of silver nanoparticles (AgNPs)

“…In continuation of our previous studies on the application of aryl glyoxals in the synthesis of heterocyclic compounds, [ 22–29 ] herein, we report a one‐pot, three‐component reaction of aryl glyoxal monohydrates, 5‐amino‐1‐aryl‐3‐methylpyrazoles, and 4‐hydroxyquinoline‐2(1 H )‐one or 2‐hydroxy‐1,4‐naphthoquinone (lawsone) using AgNPs as nanocatalyst in H 2 O/EtOH under mild conditions to afford the corresponding pyrazolonaphthyridines and pyrazoloquinolines, respectively, in good to high yields.…”

An Efficient Synthesis of Benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and Benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium Hydroxides by a One‐pot, Three‐component Reaction under Green Conditions

“…In continuation of our research on the synthesis of novel heterocyclic compounds , herein, we report an efficient synthesis of benzo[ g ]thiazolo[2,3‐ b ]quinazolin‐4‐ium and benzo[ g ]benzo[4,5]thiazolo[2,3‐ b ]quinazolin‐14‐ium hydroxides by the one‐pot, three‐component reaction of aryl glyoxal monohydrates, 2‐hydroxy‐1,4‐naphthoquinone, and 2‐aminothiazole or 2‐aminobenzothiazole using TEA/ p ‐TSA as organocatalysts in H 2 O/acetone (2:1) at room temperature.…”