Facile Synthesis and Bioactivity of Novel N,N′‐disubstituted‐1,2,3,4‐tetrahydroquinoxalines

Abstract

A series of novel N,N'‐disubstituted‐1,2,3,4‐tetrahydroquinoxalines were designed and synthesized by cyclization and acylation. The structures of all the novel compounds were confirmed by IR, 1H NMR, 13C NMR, and high‐resolution mass spectrometry. The configuration of 4d was determined by X‐ray diffraction. The preliminary biological tests showed that all the products could protect maize against the injury caused by acetochlor to some extent.

Research Progress in the Design and Synthesis of Herbicide Safeners: A Review

“…Benoxacor was used as a template, and a bioisosteric approach was used where the O atom was replaced by a N atom, and a novel compound N,N′-disubstituted 1,2,3,4-tetrahydroquinoxalines with potential herbicide safener activity was designed by Ye and Fu’s team (Scheme ). Preliminary biological activity assay results showed that N,N′-disubstituted 1,2,3,4-tetrahydroquinoxalines had excellent safety for acetochlor. Among them, compound 21 had the best effect, and corn was effectively protected from acetochlor by compound 21 .…”

Synthetic route towards 1,2,3,4-tetrahydroquinoxaline/piperidine combined tricyclic ring system

“…27 Microwave assistant reductive cyclization of substituted o-nitroaniline afforded 1,2,3,4-tetrahydroquinoxalines, as reported by Merisor et al 28 However, limitations in most cases include low yields, complicated reaction procedures and expensive catalysts. Cyclization/acylation of o-phenylenediamines with -chloroketones 29 and diboronic acid mediated cyclization/cascade transfer hydrogenation of o-phenylenediamines and o-nitroanilines with 1,2-dicarbonyl compounds, 30 are some recent examples towards more efficient synthesis of 1,2,3,4-tetrahydroquinoxalines.…”

Metal-free cascade reactions for one-pot tetrahydroquinoxaline construction through nitroarene reduction and imine hydrogenation with water

“…2,3 Compared to the hydrogenation of quinoxalinones and quinoxalines, [24][25][26][27] this method starts from raw materials and avoids the preparation of substrates, reserving elemental economy. [28][29][30] When we increase the amount of B 2 cat 2 , 1,2-dinitrobenzene can be reduced to 1,2-diaminobenzene by controlling the reaction conditions (Scheme S1, ESI †), indirectly indicating that 2-nitroaniline can also be reduced to 1,2-diaminobenzene. Therefore, we explore the feasibility of using this strategy for the one-pot synthesis of dihydroquinoxalinones.…”