A greener, efficient approach to Michael addition of barbituric acid to nitroalkene in aqueous diethylamine medium

Hany J Al-Najjar; Assem Barakat; Abdullah M Al-Majid; Yahia N Mabkhot; Manuel Weber; Hazem A Ghabbour; Hoong-Kun Fun

doi:10.3390/molecules19011150

A greener, efficient approach to Michael addition of barbituric acid to nitroalkene in aqueous diethylamine medium

Molecules. 2014 Jan 17;19(1):1150-62. doi: 10.3390/molecules19011150.

Authors

Hany J Al-Najjar¹, Assem Barakat², Abdullah M Al-Majid³, Yahia N Mabkhot⁴, Manuel Weber⁵, Hazem A Ghabbour⁶, Hoong-Kun Fun⁷

Affiliations

¹ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].
² Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].
³ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].
⁴ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].
⁵ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].
⁶ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].
⁷ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. [email protected].

Abstract

An efficient method for the synthesis of a variety of pyrimidine derivatives 3a-t by reaction of barbituric acids 1a,b as Michael donor with nitroalkenes 2a-k 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.

Publication types

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

MeSH terms

Barbiturates / chemical synthesis*
Barbiturates / chemistry
Chemistry Techniques, Synthetic
Diethylamines / chemistry*
Green Chemistry Technology
Nitro Compounds / chemistry*
Solvents / chemistry
Water / chemistry

Substances

Barbiturates
Diethylamines
Nitro Compounds
Solvents
Water
diethylamine
barbituric acid