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

• Published in: Molecules (Basel, Switzerland) Vol. 19; no. 1; pp. 1150 - 1162
• Main Authors: Al-Najjar, Hany, Barakat, Assem, Al-Majid, Abdullah, Mabkhot, Yahia, Weber, Manuel, Ghabbour, Hazem, Fun, Hoong-Kun
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 17.01.2014; MDPI
• Subjects: aqueous media; Barbiturates - chemical synthesis; Barbiturates - chemistry; barbituric acid; Chemistry Techniques, Synthetic; Diethylamines - chemistry; Electronic mail systems; green chemistry; Green Chemistry Technology; Investigations; Michael reactions; Nitro Compounds - chemistry; Solvents - chemistry; Water - chemistry; Saudi Arabia; Riyadh Saudi Arabia
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules19011150

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.