Visible-Light-Induced Preparation of Quinazolinones by Oxidation of Benzyl Alcohols in Water

doi:10.6023/cjoc202007027

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 833-841.DOI: 10.6023/cjoc202007027 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

NOTE

水相中可见光下苯甲醇氧化合成喹唑啉酮衍生物的研究

张帆^a^,^b, 侯慧青^b, 许秀枝^b, 陈志涛^b, 柯方^b^,^*()

a 福建医科大学附属第一医院肿瘤内科福州 350005
b 福建医科大学药学院福建省天然药物药理学重点实验室福州 350004

收稿日期:2020-07-09 修回日期:2020-08-20 发布日期:2020-09-16
通讯作者: 柯方
作者简介:
* Corresponding author. E-mail: kefang612@163.com
基金资助:
福建省自然科学基金(2016Y9052); 福建省自然科学基金(2016Y9053); 福建省自然科学基金(2017J01820); 福建省自然科学基金(FJNMP-201902); 福建省自然科学基金(2017-1-64)

Visible-Light-Induced Preparation of Quinazolinones by Oxidation of Benzyl Alcohols in Water

Fan Zhang^a^,^b, Huiqing Hou^b, Xiuzhi Xu^b, Zhitao Chen^b, Fang Ke^b^,^*()

a Department of Medical Oncology, The First Affiliated Hospital of Fujian Medical University, Fuzhou 350005
b Fujian Provincial Key Laboratory of Natural Medicine Pharmacolog, Department of Pharmacy, Fujian Medical University, Fuzhou 350004

Received:2020-07-09 Revised:2020-08-20 Published:2020-09-16
Contact: Fang Ke
Supported by:
the Natural Science Foundation of Fujian Province(2016Y9052); the Natural Science Foundation of Fujian Province(2016Y9053); the Natural Science Foundation of Fujian Province(2017J01820); the Natural Science Foundation of Fujian Province(FJNMP-201902); the Natural Science Foundation of Fujian Province(2017-1-64)

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Abstract

A novel visible-light-introduced reaction for the construction of quinazolinone derivatives via radical cyclization of 2-aminobenzamides with benzyl alochols under water phase has been developed. The reaction has been achieved in high yield under mild conditions by using I₂ as photocatalyst, which is cheap, available and easy to handle. A variety of quinazolinones were obtained in yields up to 92%. It might provide a promising protocol for the synthesis of quinazolinone derivatives. Its application was performed by the synthesis of N-(2-fluoro-5-methylphenyl)-6-(2,2,2-trifluoroethoxy)pteridin-4-amine, which displayed significant inhibitory activity.

Key words: visible light, Iodine, quinazolinone, oxidant, catalyst

Cite this article

Fan Zhang, Huiqing Hou, Xiuzhi Xu, Zhitao Chen, Fang Ke. Visible-Light-Induced Preparation of Quinazolinones by Oxidation of Benzyl Alcohols in Water[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 833-841.

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Fig. & Tab. 9

Figure 1. Some active molecules with quinazolinone moieties

Scheme 1. Strategies for the synthesis of quinazolinones

Entry	Solvent	Cat.	Base	T/h	Yield^b/%
1	CHCl₃	I₂	KOH	12	30
2	DMSO	I₂	KOH	12	41
3	THF	I₂	KOH	12	40
4	DMF	I₂	KOH	12	44
5	CH₂Cl₂	I₂	KOH	12	22
6	CH₃CN	I₂	KOH	12	78
7	H₂O	I₂	KOH	12	85
8^c	H₂O	Ru(bpy)₃(PF₆)₂	KOH	12	85
9^d	H₂O	Ir(bpy)₃	KOH	12	78
10^c	H₂O	Ru(bpz)₃[PF₆]₂	KOH	12	80
11	H₂O	—	KOH	12	11
12	H₂O	I₂	K₃PO₄	12	70
13	H₂O	I₂	K₂CO₃	12	73
14	H₂O	I₂	Cs₂CO₃	12	78
15	H₂O	I₂	NaOH	12	92
16	H₂O	I₂	—	12	trace
17	H₂O	I₂	NaOH	11	84
18	H₂O	I₂	NaOH	13	92
19^e	H₂O	I₂	NaOH	12	88

Table 1. Optimization of the reaction conditionsa

Table 2. Synthesis of quinazolinones

Scheme 2. Controlled experiments

. (A) O-Aminobenzamide; (B) O-aminobenzamide+NaOH+I2; (C) benzyl alcohol; (D) benzyl alcohol+I2; (E) O-aminobenzamide+benzyl alcohol+I2+NaOH

Scheme 3. Proposed mechanism for this transformation

Scheme 4. Synthesis of N-(2-fluoro-5-methylphenyl)-6-(2,2,2- trifluoroethoxy)pteridin-4-amine (D3) in water

. In vitro inhibitory data of target compounds against A549、HCT-116和SGC-7901 cell line

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水相中可见光下苯甲醇氧化合成喹唑啉酮衍生物的研究

Visible-Light-Induced Preparation of Quinazolinones by Oxidation of Benzyl Alcohols in Water

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