A Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of N- Substituted Phthalimides from Isocyanates and Benzoic Acids

被引：65

作者：

Shi, Xian-Ying ^{[1
,2
,3
]}

Renzetti, Andrea ^{[1
]}

Kundu, Soumen ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada

[2] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710062, Peoples R China

[3] Key Lab Macromol Sci Shaanxi Prov, Xian 710062, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

amidation; CH activation; cascade cyclization; isocyanates; phthalimides; rhodium; C-H BOND; ONE-STEP SYNTHESIS; CARBONYLATION REACTIONS; EFFICIENT SYNTHESIS; AROMATIC KETIMINES; CYCLIC IMIDES; IONIC LIQUID; ARYL; ACTIVATION; PALLADIUM;

D O I：

10.1002/adsc.201300834

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A rhodium(III)-catalyzed amidation between benzoic acids and isocyanates via direct functionalization of an ortho C-H bond followed by intramolecular cyclization is described. This cascade cyclization affords N-substituted phthalimides in one step in 26-91% yields. The reaction is highly atom-economical, since no theoretical waste except for water is generated in the reaction.

引用

页码：723 / 728

页数：6

共 50 条

[41] Rhodium-catalyzed one-pot synthesis of substituted pyridine derivatives from α,β-unsaturated ketoximes and alkynes
Parthasarathy, Kanniyappan
Jeganmohan, Masilamani
Cheng, Chien-Hong
ORGANIC LETTERS, 2008, 10 (02) : 325 - 328
[42] Rhodium-catalyzed tandem acylmethylation/annulation of N-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazole N-oxides
Cui, Xin-Feng
Huang, Guo-Sheng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (21) : 4014 - 4018
[43] Enantioselective Rhodium-Catalyzed Synthesis of α-Chloromethylene-γ-Butyrolactams from N-Allylic Alkynamides
Jackowski, Olivier
Wang, Jianping
Xie, Xiaomin
Ayad, Tahar
Zhang, Zhaoguo
Ratovelomanana-Vidal, Virginie
ORGANIC LETTERS, 2012, 14 (15) : 4006 - 4009
[44] Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes
Lee, Ernest E.
Rovis, Tomislav
ORGANIC LETTERS, 2008, 10 (06) : 1231 - 1234
[45] Rhodium-Catalyzed Cascade Carbene Coupling Reactions of α,α-Difluoro-N-Tosylhydrazones, Arylboronates and Alcohols for the Synthesis of Alkyl Enol Ethers
Zhao, Yueting
Wang, Xu
Li, Ran
Wang, Bingxue
Gao, Kefu
Wei, Pifeng
Hu, Fangdong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
[46] Additive-Controlled Divergent Synthesis of Fluorenone-4-carboxylic Acids and Diphenic Anhydrides via Rhodium-Catalyzed Oxidative Dimeric Cyclization of Aromatic Acids
Li, Wan-Di
Wang, Xue
Ma, Hong-Yu
Jia, Jing-Wen
Xiao, Yu-Yao
Shi, Xian-Ying
ORGANIC LETTERS, 2024, 26 (36) : 7607 - 7613
[47] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
Beenen, Melissa A.
Weix, Daniel J.
Ellman, Jonathan A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) : 6304 - 6305
[48] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
Beenen, Melissa A.
Weix, Daniel J.
Ellman, Jonathan A.
Journal of the American Chemical Society, 2006, 128 (19): : 6304 - 6305
[49] Synthesis of fully-substituted alkenylimidazoles from N-(cyanoalkyl)amides via the In-mediated allylation of nitrile and dehydrative cyclization cascade
Kim, Yu Mi
Lee, Sangku
Kim, Sung Hwan
Kim, Ko Hoon
Kim, Jae Nyoung
TETRAHEDRON LETTERS, 2010, 51 (45) : 5922 - 5926
[50] Synthesis of Highly Substituted N-(Furan-3-ylmethylene)benzenesulfonamides by a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization Cascade
Wang, Tao
Huang, Long
Shi, Shuai
Rudolph, Matthias
Hashmi, A. Stephen K.
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (45) : 14868 - 14871

← 1 2 3 4 5 →