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

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Photooxidation of 2,3-dihydroquinazolin-4(1 H )-ones: retention or elimination of 2-substitution
Molecular Diversity ( IF 3.9 ) Pub Date : 2021-01-15 , DOI: 10.1007/s11030-020-10174-3
Hamid Reza Memarian ₁ , Reza Aghalar ₁

Affiliation

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.

中文翻译：

2,3-dihydroquinazolin-4(1 H)-ones 的光氧化：保留或消除 2-取代

摘要

合成了一系列单取代和二取代的 2,3-二氢喹唑啉-4(1 H )-酮 (DHQZ)，并研究了 C ₂ - 和 N _{3 - 取代对 C}₂ -保留或消除的电子和空间效应研究了通过将它们暴露在紫外线下进行的替代。_{提出了从光激发二氢喹唑啉酮到氯仿溶剂的电子转移，其中 N 1} - 和 N ₃ - 原子上的两个孤对电子都可以参与该过程。N ₁ - 和 N ₃ -原子在该电子转移过程中的贡献程度以及 C _{2的保留或消除}-取代取决于C ₂ -和N ₃ -取代的性质和空间位阻。实验结果得到计算研究的支持。