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An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds
Molecules 2012, 17(10), 11570-11584; doi:10.3390/molecules171011570
Article

An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones

, ,  and *
Received: 10 September 2012; in revised form: 25 September 2012 / Accepted: 26 September 2012 / Published: 28 September 2012
(This article belongs to the Special Issue Organic Iodine Chemistry)
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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 iodine; microwave; 2-azetidinone; pyrrole; catalysis; green synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

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.

Chicago/Turabian Style

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.


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