Title:T3P® -DMSO Mediated One-pot Tandem Approach for the Synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones from Alcohols
Volume: 15
Issue: 4
Author(s): Kambappa Vinaya*, Prasanna D. Shivaramu, Ganganahalli K. Chandrashekara, Siddappa Chandrappa and Kanchugarakoppal S. Rangappa
Affiliation:
- Department of Chemistry, Government First Grade College, Kadur-577548,India
Keywords:
Alcohol, biginelli reaction, propylphosphonic anhydride, three-component reaction, β-ketoester, pyrimidine.
Abstract: Background: Biginelli reaction is one of the most important multiple-component chemical
reactions which creates 3,4-dihydropyrimidin-2(1H)-ones. Even though Biginelli reaction was reported
over a century using different substrates, literature lacks the example of the use of alcohols as a
substrate. The substitution of aldehyde component with another functional group has not been explored
so far.
Method: In the present study, we have used Propylphosphonic anhydride (T3P®)-DMSO as an efficient
and mild reagent for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones from
aromatic alcohols.
Results: Alcohols are oxidized in situ to aldehydes under mild conditions, which in turn undergo a
three-component reaction with β-ketoester and urea/thiourea to afford 3,4-dihydropyrimidin-2(1H)-
ones/thiones.
Conclusion: The synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones directly from alcohols has
been reported for the first time under mild reaction conditions in good yield. Easy work up procedure,
low cost and less toxicity of the reagent are the main advantages of this protocol.