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Molecules. 2018 Sep 12;23(9). pii: E2325. doi: 10.3390/molecules23092325.

"On-Water" Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile.

Author information

1
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. liuzibin1007@126.com.
2
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. Zengly2011@hotmail.com.
3
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. LC151820cg@126.com.
4
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. 15625123630@163.com.
5
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. qiufensheng1996@163.com.
6
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. liusw@smu.edu.cn.
7
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China. xibaomin@sohu.com.

Abstract

A versatile and practical "on-water" protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N₂. The protocol can be extended to other substrates and various quinazolinones and dihydroquinazolinones were obtained. o-Bromobenzamide, o-aminobenzonitrile, and o-aminobenzamide were also evaluated as starting materials, and the results further proved the versatility of this protocol, especially towards dihydroquinazolinones.

KEYWORDS:

dihydroquinazolinones; quinazolinones; selective synthesis; “on-water” reaction

PMID:
30213061
PMCID:
PMC6225144
DOI:
10.3390/molecules23092325
[Indexed for MEDLINE]
Free PMC Article

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