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Photooxidation of 2,3-dihydroquinazolin-4(1H)-ones: retention or elimination of 2-substitution

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Abstract

A series of mono and disubstituted 2,3-dihydroquinazolin-4(1H)-ones (DHQZs) were synthesized and the electronic and steric effects of the C2- and N3-substitutions on the retention or elimination of the C2-substitution by exposing them to the ultraviolet light were investigated. Electron transfer from photo-excited dihydroquinazolinones to chloroform solvent is proposed, in which both lone pairs on the N1- and N3-atoms can be involved in this process. The extent of the N1- and N3-atoms contributions in this electron-transfer process and also the retention or elimination of the C2-substitutions are dependent on the nature and steric hindrance of both C2- and N3-substitutions. The experimental results are supported by the computational studies.

Graphic abstract

Photoinduced electron-transfer reaction of a series of mono and disubstituted 2,3- dihydroquinazolin-4(1H)-ones was investigated.

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Acknowledgement

We are thankful to the Research Council and Office of Graduate Studies of the University of Isfahan for their financial support.

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  1. Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran

    Hamid Reza Memarian & Reza Aghalar

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  1. Hamid Reza Memarian
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  2. Reza Aghalar
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Correspondence to Hamid Reza Memarian.

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In memory of Prof. Dr. Dietrich Dӧpp, Universität Duisburg, Germany, who passed away on September 25, 2019.

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Memarian, H.R., Aghalar, R. Photooxidation of 2,3-dihydroquinazolin-4(1H)-ones: retention or elimination of 2-substitution. Mol Divers 26, 191–203 (2022). https://doi.org/10.1007/s11030-020-10174-3

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  • DOI: https://doi.org/10.1007/s11030-020-10174-3

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