Efficient synthesis of novel 1,2,3-triazole-linked quinoxaline scaffold via copper-catalyzed click reactions

Abstract

New 1,2,3-triazoles-linked quinoxaline, were prepared by the reaction of 2-chloro-3-(prop-2-ynyloxy)quinoxaline or 2,3-bis(prop-2-ynyloxy)quinoxaline with aromatic azides via copper-catalyzed click reactions in the presence of the Schiff base ligands.

Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold

“…We have successfully applied the copper click reaction for the construction of structures from 1,2,3-triazolelinked heterocyclic moieties. [34,35] In this study, we reported an efficient protocol for the synthesis of new 1,2,3-triazole-linked quinazoline framework (5 and 7) from the reaction of ethyl 4-oxo-3-(prop-2-yn-1-yl)-3,-4-dihydroquinazoline-2-carboxylate and related carboxamide derivatives (3) with aryl azides (4) catalyzed by copper (II) acetate, in the presence of Sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate as an efficient ligand and in water (L3) (Scheme 1).…”

“…[34,35] In this study, we reported an efficient protocol for the synthesis of new 1,2,3-triazole-linked quinazoline framework (5 and 7) from the reaction of ethyl 4-oxo-3-(prop-2-yn-1-yl)-3,-4-dihydroquinazoline-2-carboxylate and related carboxamide derivatives (3) with aryl azides (4) catalyzed by copper (II) acetate, in the presence of Sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate as an efficient ligand and in water (L3) (Scheme 1). [34,35] In this study, we reported an efficient protocol for the synthesis of new 1,2,3-triazole-linked quinazoline framework (5 and 7) from the reaction of ethyl 4-oxo-3-(prop-2-yn-1-yl)-3,-4-dihydroquinazoline-2-carboxylate and related carboxamide derivatives (3) with aryl azides (4) catalyzed by copper (II) acetate, in the presence of Sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate as an efficient ligand and in water (L3) (Scheme 1).…”

One‐pot Synthesis of Quinoxaline Chalcones from Commercially Available Calcium Carbide Through Palladium‐Catalyzed Coupling Reactions

“…Continuing our studies directed toward an efficient and straightforward synthesis of biologically active molecules based on the quinoxaline ring system, [30,31] we present an efficient strategy for the synthesis of new quinoxaline chalcones from the commercially available calcium carbide through palladiumcatalyzed coupling reactions. Our retro-synthetic analysis for the synthesis of quinoxaline chalcones showed the palladiumcatalyzed cross-coupling reaction of 2-amino substituted-3chloroqunoxalines with propargyl amine, formed in situ from calcium carbide, an aldehyde, and dimethylamine, as the key step to this process.…”

Sequential Cu‐Catalyzed Four‐ and Five‐Component Syntheses of Luminescent 3‐Triazolylquinoxalines

“…[18] The ligation of 1,2,3-triazolesa nd quinoxalines as electron-deficient moieties is particularly interesting and CuAAC [19] is as uitable methodology for introducing this moiety.H owever,t he construction of 3-triazolylquinoxalines has only been reported in two publications with very few examples. [20,21] Inspired by our chromogenic MCR concept [22] and our particular interest in highly emission solvatochromic quinoxalines, [12b, 13, 15, 23] we reasoned that 3-triazolylquinoxalines could be accessible by combining the one-pot glyoxylation-alkynylation-cyclocondensation synthesis of 3-ethynylquinoxalines with CuAACi naone-pot fashion ( Figure 1).…”