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Molecules 2014, 19(1), 1150-1162; doi:10.3390/molecules19011150
Article

A Greener, Efficient Approach to Michael Addition of Barbituric Acid to Nitroalkene in Aqueous Diethylamine Medium

1
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1,2,* , 1
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1
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3
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4
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1 Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia 2 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia- 21321 Alexandria, Egypt 3 Department of Chemistry, University of California, Berkeley, CA 94720, USA 4 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 5 December 2013 / Revised: 7 January 2014 / Accepted: 10 January 2014 / Published: 17 January 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

An efficient method for the synthesis of a variety of pyrimidine derivatives 3at by reaction of barbituric acids 1a,b as Michael donor with nitroalkenes 2ak as Michael acceptor using an aqueous medium and diethylamine is described. This 1,4-addition strategy offers several advantages, such as using an economic and environmentally benign reaction media, high yields, versatility, and shorter reaction times. The synthesized compounds were identified by 1H-NMR, 13C-NMR, CHN, IR, and MS. The structure of compound 3a was further confirmed by single crystal X-ray structure determination.
Keywords: Michael reactions; barbituric acid; aqueous media; green chemistry Michael reactions; barbituric acid; aqueous media; green chemistry
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Al-Najjar, H.J.; Barakat, A.; Al-Majid, A.M.; Mabkhot, Y.N.; Weber, M.; Ghabbour, H.A.; Fun, H.-K. A Greener, Efficient Approach to Michael Addition of Barbituric Acid to Nitroalkene in Aqueous Diethylamine Medium. Molecules 2014, 19, 1150-1162.

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