QD452 : Synthesis of new hybrid compounds from quinoxaline derivatives with other heterocyclic compounds through Pd-catalyzed reaction
Thesis > Central Library of Shahrood University > Chemistry > PhD > 2024
Authors:
Marzieh Enjilzadeh [Author], Ali Keivanloo[Supervisor], Mohammad Bakherad[Advisor]
Abstarct: New hybrid compounds including imidazo[1,2-a]pyrimidine/pyridine, baxsed on quinoxaline and 1,2,3-triazoles lixnked-imidazo[1,2-a]pyrimidine/]pyridine were synthesized through Sonogashira coupling and click reaction. Imidazo[1,2-a]pyrimidin-2-yl(3-(substituted)quinoxalin-2-yl)methanone and its imidazo[1,2-a]pyridine analogs, have been successfully prepared from the reaction of 3-substituted-2-chloroquinoxalines with 2-amino-1-(prop-2-yn-1-yl)pyrimidinium/pyridinium bromide under optimized reaction conditions. These conditions included Pd(PPh3)2Cl2 (5 mol %), CuI (10 mol%) in the presence of Et3N in DMF at 70 ºC, resulting in the formation of the desired hybrid compounds. Furthermore, imidazo[1,2-a]pyridine hybrid compounds were synthesised through one-pot multicomponent reactions of 2,3-dicholoroquinoxaline, 2-amino-1-(prop-2-yn-1-yl)pyridinium bromide, primary and secondary amines, under optimized conditions. Click reaction of 1-azido-4-iodobenzene with phenyl acetylene or propargyloxy arylaldehydes in the presence of copper(II) acetate and sodium ascorbate produced iodophenyl-1,2,3-triazoles. Subsequently, hybrid compounds 1,2,3-triazoles lixnked-imidazo[1,2-a]pyrimidine/pyridine were synthesized through the reaction of 2-amino-1-(prop-2-yn-1-yl)pyrimidinium/pyridinium bromide with iodophenyl-1,2,3-triazoles. This reaction was carried out in the presence of palladium(II) acetate and copper(I) iodide in DMF, resulting in high yields.
Keywords:
#hybrid compounds #Sonogashira coupling #Multi-component reaction #Imidazo[1 #2-a]pyrimidine #Imidazo[1 #2-a]pyridine #Quinoxaline #1 #2 #3-triazoles #click reaction. Keeping place: Central Library of Shahrood University
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