Organic Chemistry Portal

Abstracts

Search:

Metal- and Solvent-Free Approach to Diversely Substituted Picolinates via Domino Reaction of Cyclic Sulfamidate Imines with β,γ-Unsaturated α-Ketocarbonyls

Soumen Biswas, Debashis Majee, Soumitra Guin and Sampak Samanta*

*Discipline of Chemistry, Indian Institute of Technology Indore, Simrol, Indore 453552, Madhya Pradesh, India, Email: sampaksiiti.ac.in

S. Biswas, D. Majee, S. Guin, S. Samanta, J. Org. Chem., 2017, 82, 10928-10938.

DOI: 10.1021/acs.joc.7b01792 (free Supporting Information)


see article for more reactions

Abstract

DABCO promotes an efficient, solvent-free, and eco-friendly domino reaction of various β,γ-unsaturated α-ketocarbonyls with 5/6-membered cyclic sulfamidate imines in neat conditions under MW irradiation to provide densely functionalized picolinates in short reaction times.


see article for more examples

proposed mechanism



Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita-Baylis-Hillman Acetates of Nitroolefins/Nitrodienes

D. Majee, S. Biswas, S. M. Mobin, S. Samanta, J. Org. Chem., 2016, 81, 4378-4385.


Key Words

pyridines, microwave synthesis


ID: J42-Y2017