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

[21] A Rh(II)-catalyzed highly stereoselective [3+2] annulation of vinyl diazoacetates with indole-2-carbaldehyde for the synthesis of indolyl dihydrofurans
Zheng, Rimei
Xu, Aimin
Huang, Jiawu
Zhang, Zhijing
Yin, Xinru
Zhang, Tianyuan
Hu, Wenhao
Qian, Yu
MOLECULAR DIVERSITY, 2022, 26 (06) : 3379 - 3386
[22] Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates
Jing, Chengfeng
Na, Risong
Wang, Bo
Liu, Hongle
Zhang, Lei
Liu, Jun
Wang, Min
Zhong, Jiangchun
Kwon, Ohyun
Guo, Hongchao
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1023 - 1034
[23] The Synthesis of Benzazepines via Sequential [3+2]-Annulation and [3,3]-Sigmatropic Rearrangement
Luo, Fang
Wang, Wei
Xiang, Chaowei
Zeng, Linghui
Zhang, Chong
Zhang, Jiankang
Zhang, Xingxian
Shao, Jiaan
Zhu, Huajian
ORGANIC LETTERS, 2024, 26 (48) : 10224 - 10228
[24] SYNTHESIS OF 3-SUBSTITUTED 4-METHYLMERCAPTO[3,4-D]PYRIMIDINES AND 4-AMINOPYRAZOLO[3,4-D]PYRIMIDINES AND THEIR RIBOSIDES
BULYCHEV, YN
KORBUKH, IA
PREOBRAZHENSKAYA, MN
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1984, (02): : 253 - 258
[25] Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3+2)-Annulation
Goodman, C. Guy
Walker, Morgan M.
Johnson, Jeffrey S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 122 - 125
[26] Application of the phosphine catalyzed (3+2) annulation: Total synthesis of ibophyllidine
Andrews, Ian P.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[27] Copper-catalyzed oxidative dehydrogenative [3+2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles
Liu, Yan-Yun
Hu, Ming
Li, Jin-Heng
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (20): : 5806 - 5812
[28] Synthesis of Dibenzoazulene Derivatives via Pd-Catalyzed (3+2) Alkyne Annulation of Dibenzosuberenone
Ma, Zhuangzhuang
Qin, Liyuan
Shangguan, Zhichun
Shu, Yilin
Ma, Junlong
Liang, Qi
Li, Cheng
Zhang, Guanxin
Zhang, Xi-Sha
Duan, Zheng
Zhang, Deqing
CHEMCATCHEM, 2024, 16 (23)
[29] Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation
Andrews, Ian P.
Kwon, Ohyun
CHEMICAL SCIENCE, 2012, 3 (08) : 2510 - 2514
[30] Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3+2] Annulation of Enaminones with Iodonium Ylides
Zhang, Mingshuai
Chen, Longkun
Sun, Haifeng
Liu, Zhuoyuan
Huang, Jiuzhong
Yu, Fuchao
ORGANIC LETTERS, 2023, 25 (40) : 7298 - 7303

← 1 2 3 4 5 →