Intramolecular Ynamide-Benzyne (3+2) Cycloadditions

被引：9

作者：

Tawatari, Tsukasa ^{[1
]}

Kato, Ritsuki ^{[1
]}

Kudo, Riku ^{[1
]}

Takasu, Kiyosei ^{[1
]}

Takikawa, Hiroshi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 19期

基金：

日本学术振兴会;

关键词：

Benzyne; Cycloaddition; Heterocycles; Ylides; Ynamides; 1,3-DIPOLAR CYCLOADDITION; NUCLEOPHILIC-SUBSTITUTION; SELECTIVE SYNTHESIS; NITRILE OXIDES; N-ARYLINDOLES; ARYNES; EFFICIENT; NITROGEN; BENZOTRIAZOLES; 1H-INDAZOLES;

D O I：

10.1002/anie.202300907

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein intramolecular (3+2) cycloaddition reactions between ynamides as three-atom components and benzyne. In these intramolecular reactions, the two-bond formation is realized by exploiting benzyne precursors that contain a chlorosilyl group as a linking functionality. This method thus highlights the ambivalent character of the intermediate indolium ylide, which exhibits both nucleophilic and electrophilic properties at its C2 atom.

引用

页数：6

共 50 条

[21] DIASTEREOSELECTIVITY AND REGIOCONTROL IN INTRAMOLECULAR ALLYL CATION CYCLOADDITIONS - SELECTIVE FORMATION OF [3+2] OR [3+4] CYCLOADDUCTS
GIGUERE, RJ
TASSELY, SM
ROSE, MI
KRISHNAMURTHY, VV
TETRAHEDRON LETTERS, 1990, 31 (32) : 4577 - 4580
[22] Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. The fused/bridged mode
Denmark, SE
Gomez, L
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21): : 8015 - 8024
[23] [3+2] cycloadditions of aziridines mechanistical studies
Gaebert, C
Mattay, J
JOURNAL OF INFORMATION RECORDING, 1996, 23 (1-2): : 3 - 6
[24] Dearomative (3+2) Cycloadditions of Unprotected Indoles
Ryckaert, Bram
Hullaert, Jan
Van Hecke, Kristof
Winne, Johan M.
ORGANIC LETTERS, 2022, 24 (23) : 4119 - 4123
[25] Alkaloid synthesis via [3+2] cycloadditions
Pearson, WH
PURE AND APPLIED CHEMISTRY, 2002, 74 (08) : 1339 - 1347
[26] [3+2]-Cycloadditions of nitrilimines with heteroaryl thioketones
Ali, Korany A.
Mloston, Grzegorz
Urbaniak, Katarzyna
Linden, Anthony
Heimgartner, Heinz
JOURNAL OF SULFUR CHEMISTRY, 2017, 38 (06) : 604 - 613
[27] [3+2]-Cycloadditions of Azomethine Imines and Ynolates
Winterton, Sarah E.
Ready, Joseph M.
ORGANIC LETTERS, 2016, 18 (11) : 2608 - 2611
[28] BROMONITRILE OXIDE [3+2] CYCLOADDITIONS IN WATER
ROHLOFF, JC
ROBINSON, J
GARDNER, JO
TETRAHEDRON LETTERS, 1992, 33 (22) : 3113 - 3116
[29] Initial Examinations of the Diastereoselectivity and Chemoselectivity of Intramolecular Silyl Nitronate [3+2] Cycloadditions with Alkenyl/Alkynyl Nitroethers
Stevens, Katelyn
Li, Shik Ki
Kaufman, Emily
Schull, Annika
Hassebroek, Katie
Stevens, Joseph
Grandbois, Matthew
Viste, Arlen
Duffy-Matzner, Jetty
MOLECULES, 2024, 29 (24):
[30] Tandem Diels-Alder [4+2] Cycloadditions and Intramolecular [3+2] Cross-Cycloadditions of Dienylcyclopropane 1,1-Diesters
Ren, Jun
Bao, Jilai
Ma, Weiwei
Wang, Zhongwen
SYNLETT, 2014, 25 (16) : 2260 - 2264

← 1 2 3 4 5 →