铑催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的[3+3]环化合成螺吡喃化合物

doi:10.6023/cjoc202403012

有机化学 ›› 2024, Vol. 44 ›› Issue (7): 2223-2232.DOI: 10.6023/cjoc202403012 上一篇下一篇

研究论文

铑催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的[3+3]环化合成螺吡喃化合物

温梦柯^a^,^b, 李宜越^b, 杜浩康^b, 陈章培^a^,^*(), 杨西发^b^,^*()

a 东北大学理学院化学系辽宁沈阳 110819
b 河南农业大学植物保护学院农药系郑州 450002

收稿日期:2024-03-10 修回日期:2024-04-02 发布日期:2024-04-24
基金资助:
国家自然科学基金(22201066); 河南省科技攻关(222102110259)

Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones

Mengke Wen^a^,^b, Yiyue Li^b, Haokang Du^b, Zhangpei Chen^a(), Xifa Yang^b()

a Department of Chemistry, College of Sciences, Northeastern University, Shenyang, Liaoning 110819
b Department of Pesticide Science, College of Plant Protection, Henan Agricultural University, Zhengzhou, Henan 450002

Received:2024-03-10 Revised:2024-04-02 Published:2024-04-24
Contact: * E-mail: chenzhangpei@mail.neu.edu.cn;yangxifachem@163.com
Supported by:
National Natural Science Foundation of China(22201066); Science and Technology Planning Project of Henan Province(222102110259)

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摘要/Abstract

通过Rh(III)催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的1∶1偶联环化合成了一系列含NH的螺吡喃化合物, 该反应经C—H键活化随后发生[3+3]环化得到目标产物, 表现出良好的官能团耐受性. 同时, 对反应机理进行了初步探索, 并提出了相应的催化循环机理.

关键词: 螺吡喃化合物, 三价铑, 碳氢键活化, 苯并噁嗪, 重氮萘-2H-酮

Rh(III)-catalyzed 1∶1 coupling of 3-aryl-2H-benzo[b][1,4]oxazines with diazonaphthalene-2H-ones has been realized for mild synthesis of NH-containing spiropyrans. The reaction proceeded via C—H activation followed [3+3] annulation with decent functional group tolerance. Preliminary mechanistic studies have been conducted and a plausible mechanism has been proposed.

Key words: spiropyrans, Rh(III), C—H activation, benzoxazines, diazonaphthalen-2H-ones

引用此文

温梦柯, 李宜越, 杜浩康, 陈章培, 杨西发. 铑催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的[3+3]环化合成螺吡喃化合物[J]. 有机化学, 2024, 44(7): 2223-2232.

Mengke Wen, Yiyue Li, Haokang Du, Zhangpei Chen, Xifa Yang. Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2223-2232.

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图/表 5

图式1. 铑/钌催化的C—H键活化策略合成螺吡喃类化合物

Scheme 1. Synthese of spiropyran via Rh(III)/Ru(II)-catalyzed C—H activation

Entry^a^,^b	Additive (equiv.)	Solvent (2 mL)	Yield/%
1	K₂CO₃ (2.0)	PhCF₃	34
2	Na₂CO₃ (2.0)	PhCF₃	45
3	NaOAc (2.0)	PhCF₃	55
4	PivOH (2.0)	PhCF₃	55
5	LiOAc (2.0)	PhCF₃	50
6	Zn(OAc)₂ (0.2)	PhCF₃	53
7	MesCOOH (2.0)	PhCF₃	60
8	MesCOOH (2.0)	TFE	10
9	MesCOOH (2.0)	THF	42
10	MesCOOH (2.0)	1,4-Dioxane	45
11	MesCOOH (2.0)	DCM	80
12	MesCOOH (2.0)	DCE	90
13^c	MesCOOH (2.0)	DCE	Trace
14^d	MesCOOH (2.0)	DCE	Trace
15^e	MesCOOH (2.0)	DCE	13
16^f	MesCOOH (2.0)	DCE	NR
17^g	MesCOOH (2.0)	DCE	86
18^h	MesCOOH (2.0)	DCE	65

表1. C—H活化/螺环化反应条件优化a

Table 1. Optimization of the C—H activation/spiroannulation reaction conditions

表2. 苯并噁嗪与重氮萘-2H-酮的适用范围a

Table 2. Scope of the benzoxazines and diazonaphthalen-2H-ones

图式2. C—H活化/螺环化反应的机理研究

Scheme 2. Mechanistic studies of the C—H activation/spiroan- nulation reaction

图式3. C—H活化/螺环化反应可能的催化循环

Scheme 3. Possible catalytic cycle for C—H activation/spiroan- nulation reaction

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铑催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的[3+3]环化合成螺吡喃化合物

Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones

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