Novel Isocyanide-Based Three-Component Synthesis of 3,4-Dihydroquinoxalin-2-amine Derivatives

Abstract

Synthesis of a novel class of highly substituted 3,4-dihydroquinoxalin-2-amine derivatives including spirocyclic compounds from three-component condensation reaction of o-phenylenediamines, diverse carbonyl compounds, and isocyanides in the presence of a catalytic amount of p-toluenesulfonic acid in good to excellent yields at room temperature is described.

Guanidinium-based sulfonic acid as a new Brønsted acid organocatalyst in organic synthesis in water

“…The results of our catalyst with respect to the yields, solvents, temperature, and reaction times have been compared with previously reported catalysts in the synthesis of dihydroquinoxaline derivatives [32][33][34][35][36][37][38][39]. As shown in Table 3, in the case of the present work, a shorter reaction time at room temperature and minimal environmental impact are notable features of this procedure.…”

“…The chemicals used in this work were purchased from the Merck and Fluka chemical companies. All the products are known compounds and were characterized by IR and NMR spectroscopic data, and their melting points are compared with reported values [32][33][34][35][36][37][38][39][40][41][42][43][44][45]. …”

Wool-SO3H and nano-Fe3O4@wool as two green and natural-based renewable catalysts in one-pot isocyanide-based multicomponent reactions

“…As part of our ongoing program related to developing new methods using solid acids and heterogeneous catalysts in organic compound transformations [3,4,31], and based on our previous investigations on multicomponent reaction [32][33][34][35][36][37], wool-SO 3 H and Fe 3 O 4 @wool were synthesized and investigated as catalysts for the synthesis of 3,4-dihydroquinoxalin-2-amine, 1,6-dihydropyrazine-2,3-dicarbonitrile, (cyanophenylamino)acetamide, tetrahydro-1H-1,5-benzodiazepine-2-carboxamide, and 4,5,6,7-tetrahydro-1H-1,4-diazepine-5-carboxamide derivatives (Scheme 2).…”

Syntheses of 2-Deoxy-2,3-didehydro-<i>N</i>-acetylneuraminic Acid Analogues Modified by α-Acylaminoamido Groups at the C-4 Position Using Isocyanide-Based Four-Component Coupling and Biological Evaluation as Inhibitors of Human Parainfluenza Virus Type 1

“…1). For further insight into the interaction of sialidase with a substituent at C-4 of Neu5Ac2en derivatives, we herein report the synthesis of novel compounds 11 with an α-acylaminoamido group at the C-4 position of 1 using isocyanide-based four-component reaction 20) of 4-isocyano Neu5Ac2en derivative 12 as a key intermediate; we also studied their inhibitory activities against hPIV-1 sialidase (Chart 1). Ugi reactions 21) are particularly interesting as they are more versatile and diverse than other MCRs.…”