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

被引：0

作者：

Wen Mengke ^{[1
,2
]}

Li Yiyue ^{[2
]}

Du Haokang ^{[2
]}

Chen Zhangpei ^{[1
]}

Yang Xifa ^{[2
]}

机构：

[1] Northeastern Univ, Dept Chem, Coll Sci, Shenyang 110819, Liaoning, Peoples R China

[2] Henan Agr Univ, Dept Pesticide Sci, Coll Plant Protect, Zhengzhou 450002, Henan, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 44卷 / 07期

基金：

中国国家自然科学基金;

关键词：

spiropyrans; Rh(III); C-H activation; benzoxazines; diazonaphthalen-2H-ones; N-SULFONYL KETIMINES; C-H ACTIVATION; SPIROCYCLIC SULTAM; ANNULATION; SCAFFOLDS;

D O I：

10.6023/cjoc202403012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2223 / 2232

页数：10

共 49 条

[1] All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration
Burns, David J.
Best, Daniel
Wieczysty, Martin D.
Lam, Hon Wai
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) : 9958 - 9962
[2] Highly Enantioselective Hydrogenation of tetra- and tri-Substituted α,β-Unsaturated Carboxylic Acids with oxa-Spiro Diphosphine Ligands
Chen, Gen-Qiang
Huang, Jia-Ming
Lin, Bi-Jin
Shi, Chuan
Zhao, Ling-Yu
Ma, Bao-De
Ding, Xiao-Bing
Yin, Qin
Zhang, Xumu
[J]. CCS CHEMISTRY, 2020, 2 (06): : 468 - 477
[3] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
Chen, Zhengkai
Wang, Binjie
Zhang, Jitan
Yu, Wenlong
Liu, Zhanxiang
Zhang, Yuhong
[J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295
[4] C-H Activation: Toward Sustainability and Applications
Dalton, Toryn
Faber, Teresa
Glorius, Frank
[J]. ACS CENTRAL SCIENCE, 2021, 7 (02) : 245 - 261
[5] Design, synthesis and biological evaluation of 2H-benzo[b][1,4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics
Das, Bhaskar C.
Madhukumar, Ankanahlli V.
Anguiano, Jaime
Mani, Sridhar
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) : 4204 - 4206
[6] New development in the enantioselective synthesis of spiro compounds
Ding, Aishun
Meazza, Marta
Guo, Hao
Yang, Jung Woon
Rios, Ramon
[J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (15) : 5946 - 5996
[7] Rhodium-Catalyzed Spirocyclic Sultam Synthesis by [3+2] Annulation with Cyclic N-Sulfonyl Ketimines and Alkynes
Dong, Lin
Qu, Chuan-Hua
Huang, Ji-Rong
Zhang, Wei
Zhang, Qian-Ru
Deng, Jin-Gen
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) : 16537 - 16540
[8] Rh(III)-Catalyzed Successive C-H Activations of 2-Phenyl-3H-indoles and Cyclization Cascades to Construct Highly Fused Indole Heteropolycycles
Gao, Ju
Luo, Keyu
Wei, Xiaohui
Wang, Hao
Liu, Hong
Zhou, Yu
[J]. ORGANIC LETTERS, 2023, 25 (19) : 3341 - 3346
[9] Ir-SpinPHOX Catalyzed Enantioselective Hydrogenation of 3-Ylidenephthalides
Ge, Yao
Han, Zhaobin
Wang, Zheng
Feng, Chen-Guo
Zhao, Qian
Lin, Guo-Qiang
Ding, Kuiling
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13140 - 13144
[10] Recent Progress of Asymmetric Catalysis from a Chinese Perspective
He, Yan-Mei
Cheng, Yuan-Zheng
Duan, Yingdong
Zhang, Yan-Dong
Fan, Qing-Hua
You, Shu-Li
Luo, Sanzhong
Zhu, Shou-Fei
Fu, Xue-Feng
Zhou, Qi-Lin
[J]. CCS CHEMISTRY, 2023, 5 (12): : 2685 - 2716

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