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RESEARCH ARTICLE
Contents Vol 73(12)

A Facile Microwave and SnCl2 Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Nicholas S. O’Brien A and Adam McCluskey https://orcid.org/0000-0001-7125-863X A B
+ Author Affiliations
- Author Affiliations

A Chemistry, School of Environmental and Life Sciences, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia.

B Corresponding author. Email: adam.mccluskey@newcastle.edu.au

Australian Journal of Chemistry 73(12) 1176-1186 https://doi.org/10.1071/CH20101
Submitted: 25 March 2020  Accepted: 6 July 2020   Published: 24 September 2020

Abstract

An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1 % SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17–99 %. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels–Alder addition. As a result, thiophene afforded high yields (80 %) whereas pyrrole carboxaldehyde failed to react. With simple cinnamaldehydes, and in the SbCl3-mediated reaction, and with α,β-unsaturated aldehydes the equivalent quinazolin-4(3H)-ones, and not the 2,3-dihydroquinazolin-4(1H)-ones, was favoured.


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