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Caesium carbonate promoted regioselective

Vijay Kumar1, Praval Pratap Singh2, Ashish Ranjan Dwivedi1,3

  • 1Laboratory of Organic and Medicinal Chemistry, Department of Chemistry, Central University of Punjab Bathinda Punjab 151401 India vpathania18@gmail.com vinod.kumar@cup.edu.in +911642864214.

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A new catalyst-free method regioselectively functionalizes diphenylpyrimidinones. Cesium carbonate in DMF enables efficient O-alkylation, yielding 14 compounds in high yields.

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Area of Science:

  • Organic chemistry
  • Synthetic methodology
  • Heterocyclic chemistry

Background:

  • Pyrimidinone derivatives are important scaffolds in medicinal chemistry.
  • Regioselective functionalization is crucial for synthesizing targeted compounds.
  • Developing efficient and mild synthetic routes remains a key challenge.

Purpose of the Study:

  • To develop a facile, one-step, catalyst-free method for regioselective functionalization of 4,6-diphenylpyrimidin-2(1H)-ones.
  • To achieve high selectivity towards the O-regioisomer.
  • To extend the methodology to other heterocyclic systems like 2-phenylquinazolin-4(3H)-one derivatives.

Main Methods:

  • A one-step reaction employing cesium carbonate (Cs2CO3) in N,N-dimethylformamide (DMF).
  • Catalyst-free conditions under mild temperatures.
  • Density Functional Theory (DFT) calculations to study reaction mechanisms and transition states.

Main Results:

  • Successfully synthesized 14 regioselectively O-alkylated 4,6-diphenylpyrimidines with yields ranging from 81-91%.
  • Demonstrated high O-regioselectivity using Cs2CO3 in DMF without coupling reagents.
  • DFT studies confirmed the favorable transition state for O-alkylation with Cs2CO3.
  • Extended the methodology to improve the O/N ratio for alkylation of 2-phenylquinazolin-4(3H)-one derivatives.

Conclusions:

  • Developed an efficient and mild catalyst-free methodology for regioselective O-alkylation of diphenylpyrimidinones.
  • The use of Cs2CO3 is key to achieving high O-selectivity.
  • The method offers a valuable synthetic tool for accessing functionalized pyrimidine and quinazolinone derivatives.