Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

Abstract

Different benzofuran derivatives are synthesized via a catalyst-free reaction between nitroepoxides and salicylaldehydes. In the employed methodology, K2CO3 and DMF have been used at 110 °C, and the reactions were completed after 12 h in 33–84% yields. The highest yields were obtained using 3-nitrosalicylaldehyde. Finally, a plausible mechanism was proposed for the reaction, and some evidence was provided for this mechanism such as the detection of released acetate anion (using FTIR) and isolation and structure determination of the critical intermediate.

Catalyst free one pot three components synthesis of 2-iminothiazoles from nitroepoxides and thiourea

“…In addition, bis -nucleophiles such as N -alkyl(thio)ethanolamine 26 , amidines 27 , diamines 28 , S -alkyl dithiocarbamates 23 and etc. 29 – 31 have been utilized in the reaction with nitroepoxides for the synthesis of valuable heterocyclic compounds including imidazoles, 1,3-thiazoles, benzodiazepines, thiazoline-2-thiones, and pyrazines.…”

“…In addition, bis-nucleophiles such as N-alkyl(thio)ethanolamine 26 , amidines 27 , diamines 28 , S-alkyl dithiocarbamates 23 and etc. [29][30][31] have been utilized in the reaction with nitroepoxides for the synthesis of valuable heterocyclic compounds including imidazoles, 1,3-thiazoles, benzodiazepines, thiazoline-2-thiones, and pyrazines.Multicomponent reactions (MCRs) provide simple access to complex molecules in a one-pot. MCRs have several advantages such as generation of several bonds in a single operation, avoiding the need for isolation and purification of reaction intermediates, saving in time, materials, solvents and energy [32][33][34][35][36][37][38] .…”

Catalyst-Free One-Pot Three-Component Synthesis of 2-Iminothiazoles from Nitroepoxides

“…23,25 In addition, bis-nucleophiles such as N-alkyl(thio)ethanolamine, 26 amidines, 27 diamines, 28 S-alkyl dithiocarbamates 23 and etc. [29][30][31] have been utilized in the reaction with nitroepoxides for the synthesis of valuable heterocyclic compounds including imidazoles, 1,3-thiazoles, benzodiazepines, thiazoline-2-thiones, and pyrazines.…”

CuI‐catalyzed, one‐pot synthesis of 3‐aminobenzofurans in deep eutectic solvents

“…[26,27] Instead, their new generation, named as deep eutectic solvents (DESs), [28] solved the most of these problems, in addition to covering the common benefits of ILs. [29] Following the previous works of this group to develop the synthetic methodologies by using DESs [30][31][32][33] and a recent report on preparation of benzofuran derivatives, [34] the preparation of benzofuran derivatives has been considered under green media condition in this study.…”