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

doi:10.6023/cjoc202403012

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2223-2232.DOI: 10.6023/cjoc202403012 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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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References 13

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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

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

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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