- Title
- A facile microwave and SnCl2 synthesis of 2,3-dihydroquinazolin-4(1H)-ones
- Creator
- O'Brien, Nicholas S.; McCluskey, Adam
- Relation
- ARC.DP180101781 http://purl.org/au-research/grants/arc/DP180101781
- Relation
- Australian Journal fo Chemistry Vol. 73, Issue 12, p. 1176-1186
- Publisher Link
- http://dx.doi.org/10.1071/CH20101
- Publisher
- CSIRO
- Resource Type
- journal article
- Date
- 2020
- Description
- 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.
- Subject
- facile; microwave; pure material; highly tolerant; electrophilic addition; thiophene
- Identifier
- http://hdl.handle.net/1959.13/1424913
- Identifier
- uon:38165
- Identifier
- ISSN:0004-9425
- Language
- eng
- Reviewed
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