Document Type
Article
Publication Date
10-7-2013
Abstract
Pyrrole and 2-azetidinone are two essential heterocyclic scaffolds, which are being broadly used in medicinal chemistry and drug discovery field. A green and practical method to synthesize novel N-(2-azetidinonyl) 2,5-disubstituted pyrroles, which are comprised of both pyrrole and 2-azetidinone moieties, has been developed. The classical Paal–Knorr reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful pyrrole derivatives. The present procedure for the synthesis of N-(2-azetidinonyl) 2,5-disubstituted pyrroles (1,2,5-trisubstituted pyrroles) has been accomplished by reacting 3-amino β-lactams and 2,5-hexanedione in the presence of bismuth nitrate pentahydrate as an ecofriendly catalyst using microwave irradiation under solvent free condition. A comparison has also been made between the efficiency of microwave-assisted condition and the classical method (stirring at room temperature). The present method is equally effective for N-polyaromatic substituted β-lactams and optically pure β-lactams with chemically sensitive functionalities. The structure and stereochemistry of the products have been confirmed by extensive spectroscopic and X-ray crystallographic analyses. The present procedure for synthesizing N-(2-azetidinonyl) 2,5-disubstituted pyrroles may find application in the development of potent pharmacologically active molecules.
Recommended Citation
Bandyopadhyay, D., Rhodes, E., & Banik, B. K. (2013). A green, chemoselective, and practical approach toward N-(2-azetidinonyl) 2,5-disubstituted pyrroles. RSC Advances, 3(37), 16756–16764. https://doi.org/10.1039/C3RA42266F
First Page
16756
Last Page
16764
Publication Title
RSC Advances
DOI
10.1039/c3ra42266f
Comments
© 2013 Royal Society of Chemistry. Published under Creative Commons License. Original published version available at http://doi.org/10.1039/c3ra42266f.
Bandyopadhyay, D., Rhodes, E., Banik, R. A Green Chemoselective and Practical Approach Toward N-(2-Azetidinonyl) 25-Disubstituted Pyrroles. RSC Advances 2013, vol. 3, 16756-16764.