碘化铵催化sp3 C—H双胺化反应合成喹唑啉-4(3H)-酮

doi:10.6023/cjoc202203030

有机化学 ›› 2022, Vol. 42 ›› Issue (8): 2449-2455.DOI: 10.6023/cjoc202203030 上一篇下一篇

研究论文

碘化铵催化sp³ C—H双胺化反应合成喹唑啉-4(3H)-酮

喻晓哓, 柏汪恒, 朱建业, 张雨婷, 张梦茹, 吴际伟^*()

安徽科技学院化学与材料工程学院安徽凤阳 233100

收稿日期:2022-03-16 修回日期:2022-04-25 发布日期:2022-05-26
通讯作者: 吴际伟
基金资助:
安徽省自然科学基金(2008085QB66); 安徽科技学人才引进(HCYJ201903); 安徽省大学生创新创业训练计划(S202010879140)

Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds

Xiaoxiao Yu, Wangheng Bai, Jianye Zhu, Yuting Zhang, Mengru Zhang, Jiwei Wu()

College of Chemistry and Materials Engineering, Anhui Science and Technology University, Fengyang, Anhui 233100

Received:2022-03-16 Revised:2022-04-25 Published:2022-05-26
Contact: Jiwei Wu
Supported by:
Natural Science Foundation of Anhui Province(2008085QB66); Anhui Science and Technology Talent Introduction Project(HCYJ201903); Innovation and Entrepreneurship Training Program for College Students in Anhui Province(S202010879140)

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摘要/Abstract

发展了一种在廉价碘化铵为催化剂的条件下, 利用芳烃苄位sp³C—H氧化活化双胺化反应合成喹唑啉-4(3H)-酮类化合物的方法. 该反应中碘化铵作为催化剂, 过氧化氢叔丁醇(TBHP)作为氧化剂, 二甲基亚砜(DMSO)作为溶剂, 在100 ℃下反应20 h, 可以以中等到优良的产率得到喹唑啉-4(3H)-酮类化合物. 接着对该催化体系进行了机理研究和探索, 并推测了可能的反应机理. 该方法无需使用金属催化剂, 具有条件简单、底物适用范围广等优点, 因此具有潜在的工业应用的可能性.

关键词: 碘化铵催化, 喹唑啉-4(3H)-酮, sp³C—H双胺化

A novel method for synthesizing quinazoline-4(3H)-ones was developed by using inexpensive ammonium iodide as catalyst via dual amination of aromatic benzylic position sp³ C—H bonds. In this reaction, ammonium iodide was used as catalyst, tert-butanol hydrogen peroxide (TBHP) was used as oxidant and dimethyl sulfoxide (DMSO) was used as solvent. The reaction was carried out at 100 ℃ for 20 h to obtain quinazoline-4(3H)-ones compounds with moderate to excellent yields. Furthermore, the mechanism investigations were conducted, and the possible reaction mechanism was depicted. Due to the method does not require use metal catalyst, and has the advantages of simple conditions and wide substrate application range, the present protocol has the potential to be widely applied.

Key words: ammonium iodine catalysis, quinazolin-4(3H)-ones, dual amination of sp³C—H bonds

引用此文

喻晓哓, 柏汪恒, 朱建业, 张雨婷, 张梦茹, 吴际伟. 碘化铵催化sp³ C—H双胺化反应合成喹唑啉-4(3H)-酮[J]. 有机化学, 2022, 42(8): 2449-2455.

Xiaoxiao Yu, Wangheng Bai, Jianye Zhu, Yuting Zhang, Mengru Zhang, Jiwei Wu. Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2449-2455.

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碘化铵催化sp³ C—H双胺化反应合成喹唑啉-4(3H)-酮

Synthesis of Quinazolin-4(3H)-ones via Ammonium Iodide-Catalyzed Dual Amination of sp³ C—H Bonds

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Entry	Cat.	[O]	Solvent	Time/h	Yield^b/%
1	TBAI	TBHP	DMSO	20	77
2	KI	TBHP	DMSO	20	76
3	I₂	TBHP	DMSO	20	78
4	NH₄I	TBHP	DMSO	20	90
5	ZnI₂	TBHP	DMSO	20	83
6	NIS	TBHP	DMSO	20	36
7	—	TBHP	DMSO	20	0
8	NH₄Cl	TBHP	DMSO	20	0
9	NH₄I	TBHP	PhCl	20	47
10	NH₄I	TBHP	PhCH₃	20	36
11	NH₄I	TBHP	DMF	20	29
12	NH₄I	TBPB	DMSO	20	63
13	NH₄I	DTBP	DMSO	20	71
14	NH₄I	H₂O₂	DMSO	20	0
15	NH₄I	Na₂S₂O₈	DMSO	20	0
16	NH₄I	(NH₄)₂S₂O₈	DMSO	20	0
17	NH₄I	—	DMSO	20	0
18	NH₄I	TBHP	DMSO	12	53
19	NH₄I	TBHP	DMSO	16	74
20	NH₄I	TBHP	DMSO	24	90
21^c	NH₄I	TBHP	DMSO	20	63
22^d	NH₄I	TBHP	DMSO	20	87
23^e	NH₄I	TBHP	DMSO	20	76
24^f	NH₄I	TBHP	DMSO	20	90