A greener, efficient approach to Michael addition of barbituric acid to nitroalkene in aqueous diethylamine medium.
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.
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. hany_33@hotmail.com.
Hany J
HJ
Al-Najjar
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. ambarakat@ksu.edu.sa.
Assem
A
Barakat
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. amajid@ksu.edu.sa.
Abdullah M
AM
Al-Majid
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. yahia@ksu.edu.sa.
Yahia N
YN
Mabkhot
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. manuelweber@berkeley.edu.
Manuel
M
Weber
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.
Hazem A
HA
Ghabbour
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. hfun.c@ksu.edu.sa.
Hoong-Kun
HK
Fun
D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D004048:Diethylamines / Q000737:chemistry*; D055772:Green Chemistry Technology; D009574:Nitro Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry
D001463:Barbiturates; D004048:Diethylamines; D009574:Nitro Compounds; D012997:Solvents; D014867:Water; C034281:diethylamine; C032232:barbituric acid