One-Pot Synthesis of Indolizines via Sequential Rhodium-Catalyzed [2+1]-Cyclopropanation, Palladium-Catalyzed Ring Expansion, and Oxidation Reactions from Pyridotriazoles and 1,3-Dienes

被引：49

作者：

Kim, Hyunseok ^{[1
]}

Kim, Sanghyuck ^{[1
]}

Kim, Jiyeon ^{[1
]}

Son, Jeong-Yu ^{[1
]}

Baek, Yonghyeon ^{[1
]}

Um, Kyusik ^{[1
]}

Lee, Phil Ho ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem, Chunchon 24341, South Korea

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 20期

基金：

新加坡国家研究基金会;

关键词：

PYRROLE-CONTAINING HETEROCYCLES; 2-(PYRIDIN-2-YL)ACETATE DERIVATIVES; TRANSANNULATION REACTION; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; C-C; ACTIVATION; CYCLIZATION; NITRILES; ALKENES;

D O I：

10.1021/acs.orglett.7b02826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, one-pot synthetic method for producing functionalized indolizine derivatives was developed via a Rh-catalyzed [2 + 1]-cyclopropanation, Pd-catalyzed ring expansion, and subsequent Oxidation using manganese dioxide from pridotriazoles and 1,3-dienes.

引用

页码：5677 / 5680

页数：4

共 50 条

[1] Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes
Yang, Ji
Liu, Jiawang
Neumann, Helfried
Franke, Robert
Jackstell, Railf
Beller, Matthias
SCIENCE, 2019, 366 (6472) : 1514 - +
[2] Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes
Gao, Shang
Liu, Hao
Yang, Chi
Fu, Zhiyuan
Yao, Hequan
Lin, Aijun
ORGANIC LETTERS, 2017, 19 (18) : 4710 - 4713
[3] Synthesis of Dihydrobenzofurans via Palladium-Catalyzed Annulation of 1,3-Dienes by o-Iodoaryl Acetates
Rozhkov, Roman V.
Larock, Richard C.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) : 4131 - 4134
[4] Palladium-Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3-Dienes
Zou, Suchen
Zhao, Zeyu
Huang, Hanmin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (47)
[5] Rhodium-Catalyzed Cycloadditions between 3-Diazoindolin-2-imines and 1,3-Dienes
Lang, Bo
Zhu, Huangtianzhi
Wang, Chen
Lu, Ping
Wang, Yanguang
ORGANIC LETTERS, 2017, 19 (07) : 1630 - 1633
[6] Palladium-catalyzed synthesis of 3-trifluoromethylated 1,3-dienes from acrylate derivatives and BTP
Zhao, Qun
Wang, Jianjun
Besset, Tatiana
Pannecoucke, Xavier
Bouillon, Jean-Philippe
Poisson, Thomas
TETRAHEDRON, 2018, 74 (41) : 6033 - 6040
[7] Diversity-oriented synthesis of fluoroalkylated amines via the palladium-catalyzed divergent fluoroalkylamination of 1,3-dienes
Fu, Chen
Zhang, Zhaosheng
Li, Yuzhen
Gao, Dongni
Cui, Zi-Ning
Li, Zhaodong
CHEMICAL COMMUNICATIONS, 2022, 58 (37) : 5614 - 5617
[8] Synthesis of Dihydrophosphaisocoumarins through a Palladium-Catalyzed Oxidative Cyclization of Arylphosphonic Acid Monoethyl Esters with 1,3-Dienes
Son, Jeong-Yu
Kim, Hyunseok
Jeon, Woo Hyung
Baek, Yonghyeon
Seo, Boram
Um, Kyusik
Lee, Kooyeon
Lee, Phil Ho
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (18) : 3194 - 3206
[9] Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Tin and Sulfonyl Groups by Palladium-Catalyzed Regio- and Stereocontrolled Addition Reactions
Zhao, Hong
Yang, Weisen
Xie, Shiyun
Cai, Mingzhong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (04) : 831 - 836
[10] One-pot Synthesis of Alkynylated Coumarins via Rhodium-Catalyzed Annulation of Aryl Thiocarbamates with 1,3-Diynes or Terminal Alkynes
Gao, Yuan
Zeng, Fenfen
Sun, Xudong
Zeng, Minfeng
Yang, Zhen
Huang, Xianqiang
Shen, Guodong
Tan, Yongsheng
Feng, Ruokun
Qi, Chenze
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) : 1328 - 1333

← 1 2 3 4 5 →