Synthesis, Characterization and Antibacterial Activity of Substituted Quinoxaline-pyrrolidine Derivatives Catalyzed by Polymer Supported Reagents

Narasimha Reddy Y; Kondaiah S; Nagaraja Reddy G; Sreenivasulu Reddy T

Abstract

Synthesis, Characterization and Antibacterial Activity of Substituted Quinoxaline-pyrrolidine Derivatives Catalyzed by Polymer Supported Reagents

Author(s): Narasimha Reddy Y, Kondaiah S, Nagaraja Reddy G, Sreenivasulu Reddy T

An improved and economically viable process is described to prepare N-(1-(3-(2-fluorophenyl) quinoxalin-2-yl) pyrrolidin-3-yl) derivatives. Initially tert-butyl 1-(3-chloroquinoxalin-2-yl) pyrrolidin-3-yl carbamate (2) was prepared by treating of 2, 3-dichloroquinoxaline (1) with tert-butyl pyrrolidin-3-ylcarbamate and sodium carbonate in t-butanol. Tert-butyl 1-(3-chloroquinoxalin-2-yl) pyrrolidin-3-yl carbamate (2) is reacted with Bis-(diphenylphosphino)-ferrocene dichloropalladium (II), complex PdCl2 (dppf). DCM (6% mol) and substituted phenyl boronic acid is refluxed overnight in presence toluene to form tert-butyl 1-(3-(2-fluorophenyl) quinoxalin-2-yl) pyrrolidin-3-ylcarbamate and its related substituted compounds (3a-c). Deprotection of (3a-c) by TFA at 0-5°C in dichloroethane in presence of microporous tosic acid (MP-TSOH) to give 1-(3-(2-fluorophenyl) quinoxalin-2-yl) pyrrolidin-3-amine and its related compounds (4a-c). Amidation of deprotected product (4a-c) by dissolved in dichloroethane with Polymer Supported Triethylamine (PL-TEA) and respective acid chloride to obtained 1-(3-(2-fluorophenyl) quinoxalin-2-yl) pyrrolidin-3-amine derivatives (5a-d). Antibacterial activities of these compounds were studied.

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