Ligand Assisted Co(II)-Catalyzed Multicomponent Synthesis of Substituted Pyrroles and Pyridines
Subhajit Chakraborty1, Arijit Singha Mohapatra1, Subhangi Saha1
1Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur Botanic Garden, Howrah, 711103, India.
Abstract:
Herein, we describe a sustainable Co(II)-catalyzed synthesis of pyrroles and pyridines. Using a Co(II)-catalyst [CoII 2(La)2Cl2] (1 a) bearing redox-active 2-(phenyldiazenyl)-1,10-phenanthroline) (La) scaffold, various substituted pyrroles and pyridines were synthesized in good yields, taking alcohol as one of the primary feedstock. Pyrroles were synthesized by the equimolar reaction of 2-amino and secondary alcohols. A series of 2,4,6-substituted symmetrical pyridines were prepared via a three-component reaction of NH4OAc with 1 : 2.2 molar primary and secondary alcohols, respectively. Unsymmetrically substituted 2,4,6-trisubstituted, 2,4,5,6-tetrasubstituted, and 2,3,4,5,6-pentasubstituted pyridines were achieved via a multi-component coupling reaction of alcohols and NH4OAc. Catalyst 1 a showed encouraging results during the gram-scale synthesis of these N-heterocycles. Mechanistic investigation revealed synergistic involvement of cobalt metal and the ligand during the catalytic reactions.
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