PhIO as a powerful cyclizing reagent: regiospecific [3+2]-tandem oxidative cyclization of imine toward cofacially self-aggregated low molecular mass organic materials

Palash Pandit; Nirbhik Chatterjee; Samiran Halder; Sandip K Hota; Amarendra Patra; Dilip K Maiti

doi:10.1021/jo8028136

PhIO as a powerful cyclizing reagent: regiospecific [3+2]-tandem oxidative cyclization of imine toward cofacially self-aggregated low molecular mass organic materials

J Org Chem. 2009 Mar 20;74(6):2581-4. doi: 10.1021/jo8028136.

Authors

Palash Pandit¹, Nirbhik Chatterjee, Samiran Halder, Sandip K Hota, Amarendra Patra, Dilip K Maiti

Affiliation

¹ Department of Chemistry, University Colleges of Science and Technology, University of Calcutta, 92, A. P. C. Road, Kolkata-700009, India.

PMID: 19284739
DOI: 10.1021/jo8028136

Abstract

The powerful cyclization and tandem oxidation property of environmentally benign PhIO is developed for the first time, which leads to regiospecific [3+2]-tandem oxidative cyclization of imine at room temperature in rapid access to a new class of compounds, 1,2-functionalized 4,5-diarylimidazoles, in excellent yield with synthetic efficiency. Size, shape, and activity of the involved nanoreactors for the green approach built up from various surfactants are investigated. Spontaneous generation of low molecular mass self-aggregated organic materials, their cofacial one-dimensional packing, and interesting photophysical properties are reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Green Chemistry Technology
Imidazoles / chemical synthesis*
Imines / chemistry*
Indicators and Reagents
Oxidation-Reduction
Surface-Active Agents / chemistry

Substances

Imidazoles
Imines
Indicators and Reagents
Surface-Active Agents