Synthesis of Aryl Ketoamides via Aryne Insertion into lmides

被引：41

作者：

Wright, Austin C. ^{[1
]}

Haley, Christopher K. ^{[1
]}

Lapointe, Guillaume ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, 1200 East Calif Blvd,MC 101-20, Pasadena, CA 91125 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 12期

基金：

瑞士国家科学基金会; 美国国家科学基金会;

关键词：

SKELETONS;

D O I：

10.1021/acs.orglett.6b00994

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An insertion of arenes into both imides and anhydrides via reactive aryne intermediates presented. The reaction is performed under exceptionally mild conditions, and the corresponding ketoamide products are amenable to derivatization to deliver a variety of synthetically useful motifs such:as quinolones, indoles, and ketoanilines.

引用

页码：2793 / 2795

页数：3

共 50 条

[21] SYNTHESIS OF POLYCYCLICS VIA ARYNE ARYLATION REACTIONS
BIEHL, ER
KHANAPURE, SP
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (08) : 275 - 281
[22] Aryne Insertion Reactions into σ-Bonds
Yoshida, Hiroto
Ohshita, Joji
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (08) : 877 - 888
[23] Synthesis of novel fluorescent 12a-aryl substituted indoxylisoquinolines via aryne-induced domino process
Varlamov, A. V.
Guranova, N. I.
Novikov, R. A.
Ilyushenkova, V. V.
Khrustalev, V. N.
Baleeva, N. S.
Borisova, T. N.
Voskressensky, L. G.
RSC ADVANCES, 2016, 6 (15): : 12642 - 12646
[24] Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion
Venkatesh, Telugu
Mainkar, Prathama S.
Chandrasekhar, Srivari
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (08) : 2192 - 2198
[25] Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
Jones, Elizabeth P.
Jones, Peter
White, Andrew J. P.
Barrett, Anthony G. M.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1570 - 1576
[26] Synthesis of hyperbranched poly(aryl amine)s via a carbene insertion approach
Blencowe, Anton
Fagour, William
Blencowe, Chris
Cosstick, Kevin
Hayes, Wayne
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (13) : 2327 - 2333
[27] Synthesis of hyperbranched poly(aryl ether)s via carbene insertion processes
Blencowe, Anton
Caiulo, Nick
Cosstick, Kevin
Fagour, William
Heath, Peter
Hayes, Wayne
MACROMOLECULES, 2007, 40 (04) : 939 - 949
[28] Synthesis of α-Ketoamides via Gold(I) Carbene Intermediates
Wu, Zuo Zuo
Adak, Tapas
Dietl, Martin C.
Wang, Tao
Hu, Chao
Shi, Hongwei
Kraemer, Petra
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
ORGANIC LETTERS, 2022, 24 (24) : 4349 - 4353
[29] A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation
Allan, Kevin M.
Stoltz, Brian M.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (51) : 17270 - +
[30] Synthesis of N-Aryl α-Ketoamides, α-Ketoesters, α-Ketothioesters and Their Applications in Quinoxalinone Preparation
Singh, Shweta
Sureshbabu, Popuri
Sabiah, Shahulhameed
Kandasamy, Jeyakumar
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (05)

← 1 2 3 4 5 →