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Synlett 2012; 23(7): 1057-1063
DOI: 10.1055/s-0031-1290492
DOI: 10.1055/s-0031-1290492
letter
Photoinduced Elimination in 2,3-Dihydro-2-tert-butyl-3-benzyl-4(1H)-quinazolinone: Theoretical Calculations and Radical Trapping Using TEMPO Derivatives
Further Information
Publication History
Received: 30 December 2011
Accepted after revision: 10 February 2012
Publication Date:
29 March 2012 (online)
Abstract
Photochemical irradiation of 2,3-dihydro-2-tert-butyl-3-benzyl-4(1H)-quinazolinone produced 3-benzyl-4(3H)-quinazolinone through photoinduced elimination via a radical mechanism. The use of photochemical conditions such as chloroform and UV irradiation (λ = 254 nm) got the 3-benzyl-4(3H)-quinazolinone in a high yield. Some theoretical calculations were achieved to explain the mechanism and the presence of radical intermediates was confirmed by trapping with different 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) derivatives.
Key words
2,3-dihydro-4(1H)-quinazolinones - mechanism - photochemical reaction - 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) - AIM - MO analysis - density analysisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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