Photooxidation Coupled Kabachnik–Fields and Bigenelli reactions for Direct Conversion of Benzyl alcohols to α-Amino Phosphonates and Dihydropyrimidones.

Authors

  • Gazunfor Ali National Institute Of Technology, Srinagar
  • Nisar A Dangroo National Institute Of Technology, Srinagar
  • Shabnam Raheem Kashmir University
  • Tahira Naqvi Kashmir University
  • Tabassum Ara Department of Chemistry National Institute of Technology, Srinagar, J & K, India 190006.
  • Masood Ahmad Rizvi Kashmir University

DOI:

https://doi.org/10.17344/acsi.2019.5348

Keywords:

One-pot synthesis, photo-oxidation, benzyl alcohol, Kabachnik-Field, Biginelli reaction

Abstract

A tandem one-pot solvent free approach for the direct conversion of benzyl alcohols to α-amino phosphonates and dihydropyrimidones is reported. The method relies on a metal free photo-oxidation of benzyl alcohols to benzaldehydes under UV irradiation using ammonium perchlorate followed by Kabachnik–Fields and Biginelli reactions. The reaction conditions are moderate and metal free with good substrate scope. The control experiments were performed to investigate the role of the ammonium perchlorate and molecular oxygen as oxidants. The quenching experiments in the presence of TEMPO and other radical quenchers suggest radical based mechanism.

Author Biographies

Nisar A Dangroo, National Institute Of Technology, Srinagar

Post-doctorate
Department of Chemistry (Organic Chemistry Division)
National Institute of Technology, Srinagar, J & K, India 190006.

Tabassum Ara, Department of Chemistry National Institute of Technology, Srinagar, J & K, India 190006.

Professor

Department of Chemistry 

National Institute of Technology, Srinagar, J & K, India 190006.

Masood Ahmad Rizvi, Kashmir University

Assistant Professor

DEpartment of Chemitry, University of Kashmir    190006

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Published

20.03.2020

Issue

Vol. 67 No. 1 (2020)

Section

Organic chemistry

License

Except where otherwise noted, articles in this journal are published under the Creative Commons Attribution 4.0 International License