Synthesis of 1H‐Thiopyrano[4,3‐c]quinoline Scaffold via One‐pot Three‐component Cyclization

Abstract

A convenient and effective one‐pot synthetic method for functionalized 1H‐thiopyrano[4,3‐c]quinoline scaffold via three‐component cyclization is described. This procedure contains the reaction between 2‐chloroquinoline‐3‐carbaldehyde and 2 equivalents of phenacyl thiocyanate in the presence of triethylamine in absolute ethanol at room temperature with good yield. This eco‐friendly method has advantages such as reduction of waste, short synthetic procedure, and little amount of required reagents.

Efficient Synthesis of Highly Substituted N‐Arylamino quinolone‐based Pyrrolo[3,4‐b]pyridines and Pyrazolone‐based Pyrrolo[3,4‐b]pyridines Through a One‐Pot Three‐Component Reaction

“…The structures of the synthesized compounds were characterized by FT-IR, mass spectrometry, elemental analysis, and NMR. Unfortunately, 13 C NMR analysis for derivative 4 f was not performed due to its low solubility in analytical solvents. The spectral data for derivative 4 i show two stereoisomers, each of which has a ratio of 66 : 34.…”

“…IR spectra were recorded as KBr pellets on a Nicolet FTIR 100 spectrophotometer. 1 H NMR (300 MHz) and 13 C{ 1 H} NMR (75 MHz) spectra were General procedure for the preparation of α-aminomaleimides (3): α-Aminomaleimides 3 were synthesized using the known literature procedure. [25] The mixture of MeOH (3 mL), arylamines (1 mmol), and dimethyl acetylenedicarboxylate (1 mmol) was kept at room temperature with stirring for 10 min.…”

“…Supporting information includes experimental details, analysis data, copies of IR, 1 H, 13 C NMR and Mass spectra of products, crystal structure determination, and refinement.…”

“…Our group has also shown great interest in the synthesis of heterocyclic compounds based on quinolines such as benzo[h]pyrano [2,3-b]quinolones [12] and thiopyrano[4,3c]quinolones. [13] Recently, we have reported the synthesis of arylamino-3,5biquinolines by combining 2-chloro-3-formylquinolones with a,a-dicyanoolefines under mild conditions (ultrasound) without using metallic reagents. The impressive fluorescence properties of the synthesized heterocycles also led us to investigate their biological (anti-cancer) properties in vitro, and fortunately, we achieved acceptable results.…”

Synthesis of isomeric 4-(N-methyltetrazolylamino)-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehydes and 4-hydroxy-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehyde based on tandem thiol-Michael and (aza)-Morita–Baylis–Hillman reactions and an in vitro study of the activity of the obtained compounds against influenza virus

“… 1 , 2 It is also known that thiopyrano[2,3- b ]quinolines act as antagonists of metabotropic glutamate receptors and strong antioxidants that prevent oxidative DNA damage caused by free radicals. 3 – 5 It was recently shown that some nonannulated polynuclear heterocyclic compounds containing the tetrazol-2-yl and pyrimidine fragments in the molecule exhibit pronounced activity against dangerous influenza A varieties. 6 However, the relationship between the chemical structure, including the regioisomeric nature of the N -substituted tetrazole ring, as well as the nature of the substituent at the endocyclic carbon atom, and the antiviral activity is not adequately disclosed.…”