Iodine-Promoted Intermolecular Cyclization for the Synthesis of 2-Phenylquinazolines

doi:10.6023/cjoc202410019

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 2157-2162.DOI: 10.6023/cjoc202410019 Previous Articles Next Articles

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碘促进分子间环化合成2-苯基喹唑啉

马豪杰^a^,^*(), 周风院^a, 何雨蒙^a, 周小强^b, 孙洲^c^,^*(), 张玉琦^a^,^*()

^a 延安大学化学与化工学院陕西省化学反应工程重点实验室陕西延安 716000
^b 渭南师范学院化学与材料学院陕西渭南 714099
^c 陕西省生物农业研究所陕西省植物线虫学重点实验室西安 710043

收稿日期:2024-10-28 修回日期:2025-01-02 发布日期:2025-01-24
通讯作者: 马豪杰, 孙洲, 张玉琦
基金资助:
国家自然科学基金(31701679); 陕西省科学技术协会青年人才托举计划(20220609); 延安市科技计划(2022SLSFGG-005); 陕西省教育厅自然科学专项研究基金(23JK0432); 及陕西高校青年创新团队资助项目

Iodine-Promoted Intermolecular Cyclization for the Synthesis of 2-Phenylquinazolines

Haojie Ma^a^,^*(), Fengyuan Zhou^a, Yumeng He^a, Xiaoqiang Zhou^b, Zhou Sun^c^,^*(), Yuqi Zhang^a^,^*()

^a Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000
^b College of Chemistry and Material, Weinan Normal University, Weinan, Shaanxi 714099
^c Shaanxi Key Laboratory of Plant Nematology, Bio-Agriculture Institute of Shaanxi, Xi'an 710043

Received:2024-10-28 Revised:2025-01-02 Published:2025-01-24
Contact: Haojie Ma, Zhou Sun, Yuqi Zhang
Supported by:
National Natural Science Foundation of China(31701679); Young Talent Fund of Association for Science and Technology in Shaanxi Province(20220609); Yan'an Science and Technology Planning Project(2022SLSFGG-005); Scientific Research Program Funded by Shaanxi Provincial Education Department(23JK0432); Youth Innovation Team of Shaanxi Universities

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Abstract

Quinazolines are an important class of nitrogen-containing heterocyclic compounds, which are widely used in pharmaceuticals, biomarkers and materials science. A novel and efficient method for the synthesis of 2-phenylquinazolines through iodine-promoted intramolecular cyclization of N-(2-acetylphenyl)benzamide and cyanamide has been developed. This method has advantages of not using metal catalysts, simple operation with cheap reagents and step economy, offering a useful and attractive route for the synthesis of 2-phenylquinazolines and their derivatives.

Key words: iodine, 2-phenylquinazoline, metal-free, intermolecular cyclization

Cite this article

Haojie Ma, Fengyuan Zhou, Yumeng He, Xiaoqiang Zhou, Zhou Sun, Yuqi Zhang. Iodine-Promoted Intermolecular Cyclization for the Synthesis of 2-Phenylquinazolines[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2157-2162.

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References 38

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Entry	Solvent	I₂/equiv.	Temp./℃	Atmosphere	Yield^b/%
1	DMSO	0.5	110	N₂	20
2	DMSO	0.5	110	O₂	35
3	DMSO	0.5	110	Air	50
4	Ethanol	0.5	110	Air	20
5	MeCN	0.5	110	Air	32
6	DMF	0.5	110	Air	n.d.
7	DMSO	0.1	110	Air	Trace
8	DMSO	0.3	110	Air	25
9	DMSO	1	110	Air	Trace
10	DMSO	0.5	90	Air	15
11	DMSO	0.5	130	Air	32
12^c	DMSO	0.5	110	Air	20
13^d	DMSO	0.5	110	Air	70
14^e	DMSO	0.5	110	Air	46
15^f	DMSO	0.5	110	Air	35

Entry	Solvent	I₂/equiv.	Temp./℃	Atmosphere	Yield^b/%
1	DMSO	0.5	110	N₂	20
2	DMSO	0.5	110	O₂	35
3	DMSO	0.5	110	Air	50
4	Ethanol	0.5	110	Air	20
5	MeCN	0.5	110	Air	32
6	DMF	0.5	110	Air	n.d.
7	DMSO	0.1	110	Air	Trace
8	DMSO	0.3	110	Air	25
9	DMSO	1	110	Air	Trace
10	DMSO	0.5	90	Air	15
11	DMSO	0.5	130	Air	32
12^c	DMSO	0.5	110	Air	20
13^d	DMSO	0.5	110	Air	70
14^e	DMSO	0.5	110	Air	46
15^f	DMSO	0.5	110	Air	35

碘促进分子间环化合成2-苯基喹唑啉

Iodine-Promoted Intermolecular Cyclization for the Synthesis of 2-Phenylquinazolines

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