Synthesis of Isochromeno[3,4-d]imidazoles via Rh(II)-catalyzed [3+2] Annulation between 4-Diazoisochroman-3-imines and Oximes

被引：0

作者：

Qi, Minghui ^{[1
]}

Suleman, Muhammad ^{[1
]}

Wang, Yingxiao ^{[1
]}

Lu, Ping ^{[1
]}

Wang, Yanguang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 10期

基金：

中国国家自然科学基金;

关键词：

diazo compounds; annulation; metal carbenes; Rh(II) catalysis; ORGANIC-SYNTHESIS; IONIC LIQUIDS; IMIDAZOLES;

D O I：

10.1002/ajoc.202300343

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of isochromeno[3,4-d]imidazoles were synthesized in good yields via Rh(II)-catalyzed [3+2] annulation between 4-diazoisochroman-3-imines and oximes. This method involves the formation of rhodium carbene intermediates and elucidates the unique reactivity of oximes under Rh(II) catalysis. Operationally simple and mild reaction conditions with broad substrate diversity, and readily accessible starting materials and rhodium catalyst are the merits of our reaction.

引用

页数：6

共 50 条

[31] Synthesis of Indenones through Rhodium(III)-catalyzed [3+2] Annulation Utilizing a Recyclable Carbazolyl Leaving Group
Ochiai, Shiho
Sakai, Asumi
Usuki, Yoshinosuke
Kang, Bubwoong
Shinada, Tetsuro
Satoh, Tetsuya
CHEMISTRY LETTERS, 2021, 50 (04) : 585 - 588
[32] Gold-Catalyzed Synthesis of Bicyclo[3.2.0]heptenes via a Formal [3+2]/[2+2]-Annulation of Allylsilane with 4-Methoxybut-2-yn-1-ols
Yang, Chun-Yao
Wang, Chiou-Dong
Tian, Shu-Fan
Liu, Rai-Shung
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) : 1605 - 1609
[33] Base-mediated [3+2] annulation of trifluoroacetimidoyl chlorides and isocyanides: An improved approach for regioselective synthesis of 5-trifluoromethyl-imidazoles
Hu, Sipei
Yang, Hefei
Chen, Zhengkai
Wu, Xiao-Feng
TETRAHEDRON, 2020, 76 (19)
[34] Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes via a Tandem Dirhodium(II)-Catalyzed Triazole Denitrogenation and [3+2] Cycloaddition
Yuan, Hao
Gong, Jianxian
Yang, Zhen
ORGANIC LETTERS, 2016, 18 (21) : 5500 - 5503
[35] Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O-Spiroketal and Spiroketal
Cheng, Wen-Fu
Gao, Shan-Zeng
Yang, Yu-Chen
Wang, Lijia
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (44)
[36] Rh(III)-Catalyzed [3+2] Annulation of Aniline Derivatives with Vinylsilanes via C-H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives
Khake, Shrikant M.
Chatani, Naoto
ACS CATALYSIS, 2021, 11 (19): : 12375 - 12383
[37] 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
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) : 16537 - 16540
[38] Synthesis of 3,4-disubstituted cinnolines by the Pd-catalyzed annulation of 2-iodophenyltriazenes with an internal alkyne
Zhu, Chuan
Yamane, Motoki
TETRAHEDRON, 2011, 67 (26) : 4933 - 4938
[39] Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinoline and Ethyl (Z)-3-Acetoxy-3-tosylpent-4-enoate through Tertiary-Amine-Catalyzed [3+2] Annulation
Lei, Yu
Xing, Jiao-Jiao
Xu, Qin
Shi, Min
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (21) : 3486 - 3490
[40] Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF3-α-Amino Carboxylates
Vorobyeva, Daria V.
Petropavlovskikh, Dmitry A.
Godovikov, Ivan A.
Dolgushin, Fedor M.
Osipov, Sergey N.
MOLECULES, 2022, 27 (23):

← 1 2 3 4 5 →