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An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones
Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78539, USA
Undergraduate research participant.
* Author to whom correspondence should be addressed.
Received: 10 September 2012; in revised form: 25 September 2012 / Accepted: 26 September 2012 / Published: 28 September 2012
Abstract: 2-Azetidinones and pyrroles are two highly important classes of molecules in organic and medicinal chemistry. A green and practical method for the synthesis of 3-pyrrole-substituted 2-azetidinones using catalytic amounts of molecular iodine under microwave irradiation has been developed. Following this method, a series of 3-pyrrole- substituted 2-azetidinones have been synthesized with a variety of substituents at N-1 and at C-4. The procedure is equally effective for mono- as well as polyaromatic groups at the N-1 position of the 2-azetidinone ring. The C-4 substituent has no influence either on the yield or the rate of the reaction. Optically pure 3-pyrrole-substituted 2-azetidinones have also been synthesized following this methodology. No deprotection/rearrangement has been identified in this process, even with highly acid sensitive group-containing substrates. A plausible mechanistic pathway has also been suggested based on the evidence obtained from 1H-NMR spectroscopy. The extreme rapidity with excellent reaction yields is believed to be the result of a synergistic effect of the Lewis acid catalyst (molecular iodine) and microwave irradiation.
Keywords: iodine; microwave; 2-azetidinone; pyrrole; catalysis; green synthesis
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MDPI and ACS Style
Bandyopadhyay, D.; Cruz, J.; Yadav, R.N.; Banik, B.K. An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones. Molecules 2012, 17, 11570-11584.
Bandyopadhyay D, Cruz J, Yadav RN, Banik BK. An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones. Molecules. 2012; 17(10):11570-11584.
Bandyopadhyay, Debasish; Cruz, Jessica; Yadav, Ram N.; Banik, Bimal K. 2012. "An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones." Molecules 17, no. 10: 11570-11584.