Gold-Catalyzed β-Regioselective Formal [3+2] Cycloaddition of Ynamides with Pyrido[1,2-b]indazoles: Reaction Development and Mechanistic Insights

被引：38

作者：

Yu, Yinghua ^{[1
]}

Chen, Gui ^{[1
]}

Zhu, Lei ^{[1
]}

Liao, Yun ^{[1
,2
]}

Wu, Yufeng ^{[1
,2
]}

Huang, Xueliang ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Coal Ethylene Glycol & Its Related Techno, Fujian Inst Res Struct Matter, Yangqiao West Rd 155, Fuzhou 350002, Fujian, Peoples R China

[2] Fuzhou Univ, Coll Chem, Fuzhou 350108, Fujian, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 18期

关键词：

NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; INTERMOLECULAR NITRENE TRANSFER; PROTON-ABSTRACTION MECHANISM; INTRAMOLECULAR ARYLATION; SKELETAL REARRANGEMENT; SELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; PROPARGYL ALCOHOLS; TERMINAL ALKYNES;

D O I：

10.1021/acs.joc.6b01948

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here, we report an unprecedented gold(I)-induced beta-site regioselective formal [3 + 2] cycloaddition of ynamides with pyrido[1,2-b]indazoles, giving 3-amido-7-(pyrid-2'-yl)indoles in good to excellent yields. A complex of gold(I) catalyst with ynamide was isolated and characterized by X-ray diffraction analysis for the first time. Mechanistic investigations suggest the reaction pathway involves a gold-stabilized carbocation intermediate, which in turn participated in sequential C-H bond functionalization of the ortho-position of the phenyl ring.

引用

页码：8142 / 8154

页数：13

共 50 条

[1] Synthesis of Pyrido[1,2-b]indazoles via Aryne [3+2] Cycloaddition with N-Tosylpyridinium Imides
Zhao, Jingjing
Wu, Chunrui
Li, Pan
Ai, Wenying
Chen, Hongli
Wang, Chaojie
Larock, Richard C.
Shi, Feng
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16): : 6837 - 6843
[2] Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles
Zhou, Ai-Hua
He, Qiao
Shu, Chao
Yu, Yong-Fei
Liu, Shuang
Zhao, Tian
Zhang, Wei
Lu, Xin
Ye, Long-Wu
CHEMICAL SCIENCE, 2015, 6 (02) : 1265 - 1271
[3] Atom-Economic Synthesis of Fully Substituted 2-Aminopyrroles via Gold-Catalyzed Formal [3+2] Cycloaddition between Ynamides and Isoxazoles
Xiao, Xin-Yu
Zhou, Ai-Hua
Shu, Chao
Pan, Fei
Li, Ting
Ye, Long-Wu
CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (09) : 1854 - 1858
[4] Gold-Catalyzed Formal [3+2] Cycloaddition of Ynamides with 4,5-Dihydro-1,2,4-oxadiazoles: Synthesis of Functionalized 4-Aminoimidazoles
Xu, Wei
Wang, Gaonan
Sun, Ning
Liu, Yuanhong
ORGANIC LETTERS, 2017, 19 (12) : 3307 - 3310
[5] Gold-catalyzed intermolecular formal (3+2) cycloaddition of stabilized vinyldiazo derivatives and electronically unbiased allenes
Lopez, Enol
Lonzi, Giacomo
Gonzalez, Javier
Lopez, Luis A.
CHEMICAL COMMUNICATIONS, 2016, 52 (60) : 9398 - 9401
[6] Gold-Catalyzed [3+2]/Retro-[3+2]/[3+2] Cycloaddition Cascade Reaction of N-Alkoxyazomethine Ylides
Sugita, Shoichi
Takeda, Norihiko
Tohnai, Norimitsu
Miyata, Mikiji
Miyata, Okiko
Ueda, Masafumi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2469 - 2472
[7] Access to 1,2-Dihydroisoquinolines through Gold-Catalyzed Formal [4+2] Cycloaddition
Xin, Zhuo
Kramer, Soren
Overgaard, Jacob
Skrydstrup, Troels
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (26) : 7926 - 7930
[8] Gold-catalyzed chemoselective formal (3+2)-Annulation reaction between β-naphthols and methyl aryldiazoacetate
Harada, Shingo
Sakai, Chigaya
Tanikawa, Koki
Nemoto, Tetsuhiro
TETRAHEDRON, 2019, 75 (26) : 3650 - 3656
[9] Regioselective synthesis of novel and diverse naphtho[1,2-b]furan-3-carboxamides and benzofuran-3-carboxamides by cascade formal [3+2] cycloaddition
Xia, Likai
Lee, Yong Rok
RSC ADVANCES, 2014, 4 (69): : 36905 - 36916
[10] Mechanistic Insights into the Ru(II)-Catalyzed Intramolecular Formal [3+2] Cycloaddition of (E)-1,6-Enynes
Liu, Rui
Chou, Yajie
Lian, Bing
Fang, De-cai
Gao, Ming
Cheng, Tanyu
Liu, Guohua
ORGANIC LETTERS, 2019, 21 (17) : 6815 - 6820

← 1 2 3 4 5 →