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 usin...
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| Published in | Molecules (Basel, Switzerland) Vol. 19; no. 1; pp. 1150 - 1162 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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17.01.2014
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| 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. |
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| AbstractList | 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
1
H-NMR,
13
C-NMR, CHN, IR, and MS. The structure of compound
3a
was further confirmed by single crystal X-ray structure determination. 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.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. 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. |
| Author | Weber, Manuel Fun, Hoong-Kun Barakat, Assem Al-Majid, Abdullah Al-Najjar, Hany Ghabbour, Hazem Mabkhot, Yahia |
| AuthorAffiliation | 2 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia- 21321 Alexandria, Egypt 1 Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia; E-Mails: hany_33@hotmail.com (H.J.A.-N.); amajid@ksu.edu.sa (A.M.A.-M.); yahia@ksu.edu.sa (Y.N.M.) 4 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia; E-Mails: ghabbourh@yahoo.com (H.A.G.); hfun.c@ksu.edu.sa (H.-K.F.) 3 Department of Chemistry, University of California, Berkeley, CA 94720, USA; E-Mail: manuelweber@berkeley.edu |
| AuthorAffiliation_xml | – name: 2 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia- 21321 Alexandria, Egypt – name: 3 Department of Chemistry, University of California, Berkeley, CA 94720, USA; E-Mail: manuelweber@berkeley.edu – name: 4 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia; E-Mails: ghabbourh@yahoo.com (H.A.G.); hfun.c@ksu.edu.sa (H.-K.F.) – name: 1 Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia; E-Mails: hany_33@hotmail.com (H.J.A.-N.); amajid@ksu.edu.sa (A.M.A.-M.); yahia@ksu.edu.sa (Y.N.M.) |
| Author_xml | – sequence: 1 givenname: Hany surname: Al-Najjar fullname: Al-Najjar, Hany – sequence: 2 givenname: Assem orcidid: 0000-0002-7885-3201 surname: Barakat fullname: Barakat, Assem – sequence: 3 givenname: Abdullah surname: Al-Majid fullname: Al-Majid, Abdullah – sequence: 4 givenname: Yahia orcidid: 0000-0002-9762-0323 surname: Mabkhot fullname: Mabkhot, Yahia – sequence: 5 givenname: Manuel surname: Weber fullname: Weber, Manuel – sequence: 6 givenname: Hazem orcidid: 0000-0002-1011-0276 surname: Ghabbour fullname: Ghabbour, Hazem – sequence: 7 givenname: Hoong-Kun surname: Fun fullname: Fun, Hoong-Kun |
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| Snippet | 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... 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... 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... |
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| SubjectTerms | 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 |
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| Title | A Greener, Efficient Approach to Michael Addition of Barbituric Acid to Nitroalkene in Aqueous Diethylamine Medium |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/24445342 https://www.proquest.com/docview/1531984180 https://www.proquest.com/docview/1492681393 https://pubmed.ncbi.nlm.nih.gov/PMC6271361 https://doaj.org/article/18f21eeea56c45cf9c780766dd63307a |
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