An efficient catalyst-free protocol for the synthesis of quinoxaline derivatives under ultrasound irradiation

Abstract

Um método altamente eficiente e simples foi descrito para a síntese de derivados de quinoxalina em bons a excelentes rendimentos (80-99%) por reação de condensação de 1,2-dicetonas heterocíclicas ou alifáticas (R 1 COCOR 1 , R 1 = Et, Ph, p-MeC 6 H 5 , p-MeOC 6 H 5 , Furil) com 1,2-diaminas (1,2-(NH 2 ) 2 C 6 H 3 R 2 , R 2 = H, Br, NO 2 , PhCO). Um estudo sistemático foi realizado para examinar a influência do meio reacional e dos fatores eletrônicos dos substratos nos resultados das reações.A highly efficient and facile method has been described for the synthesis of quinoxaline derivatives in good to excellent yields (80-99%) by condensation reaction of heterocyclic as well as aliphatic 1,2-diketones (R 1 COCOR 1 , R 1 = Et, Ph, p-MeC 6 H 5 , p-MeOC 6 H 5 , Furyl) with 1,2-diamines (1,2-(NH 2 ) 2 C 6 H 3 R 2 , R 2 = H, Br, NO 2 , PhCO). A systematic study was carried out to examine the influence of reaction media and electronic factors of the substrates on the reaction results.

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

“…1 (34) through the condensation of 1,2-diarylethanediones with o-phenylenediamine by employing ultrasound irradiation as the energy source (37). The diarylethanediones were prepared by Friedel-Crafts acylation followed by SeO 2 oxidation under microwave irradiation (36).…”

Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

“…Guo et al described a highly efficient (80-99 % yield) and facile method for the condensation reaction of heterocyclic as well as aliphatic 1,2-diketones with 1,2-diamines. [64] The ultrasoundpromoted synthesis of rhodanine derivatives, of potential pharmacological and biological interest, was explored by Rostamnia and Lamei. [65] The reaction was performed in water by simple mixing of dimethyl or ethyl acetylenedicarboxylate, carbon disulfide, and an amine; products were isolated in high yields (86-94 %) and in short reaction times (3-5 min) by straightforward filtration (Scheme 19).…”

Silica Boron Sulfonic Acid as a New and Efficient Catalyst for the Green Synthesis of Quinoxaline Derivatives at Room Temperature

“…The condensation has also been accomplished under catalyst-free conditions, but this needs microwave heating [22] in industry. An efficient catalyst-free protocol for the synthesis of quinoxaline derivatives was reported under ultrasound irradiation [23]. In recent years, significant articles have appeared reporting solid-state reactions by grinding [24][25].…”