Synthesis of 2-(3-Arylallylidene)-3-oxindoles via Dirhodium(II)-Catalyzed Reaction of 3-Diazoindolin-2-imines with 1-Aryl-Substituted Allylic Alcohols and Computational Insights

被引：10

作者：

Gao, Ke ^{[1
]}

Kou, Luyao ^{[1
]}

Fu, Rui ^{[1
]}

Bao, Xiaoguang ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Rhodium catalysis; alpha-Imino carbene; Oxindole; DFT calculation; INITIATED CLAISEN REARRANGEMENT; MEROCYANINE DYES; CATALYZED REACTION; TERMINAL ALKYNES; RHODIUM; FUNCTIONALIZATION; COPPER; INDOLES; CYCLOADDITION; ACCESS;

D O I：

10.1002/adsc.201901160

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A straightforward approach for the synthesis of 2-(3-arylallylidene)-3-oxindoles has been achieved by the dirhodium(II)-catalyzed reaction of 3-diazoindolin-2-imines with 1-aryl-substituted allylic alcohols. This protocol employs easily accessible feedstocks to produce oxindole derivatives, which might be applicable in the dye industry. DFT calculations were carried out to gain a mechanistic insight into the reaction.

引用

页码：1292 / 1297

页数：6

共 50 条

[41] Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water
Wang, Xiaogang
Zhang, Jin
He, Yuan
Chen, Di
Wang, Chao
Yang, Fangzhou
Wang, Weitao
Ma, Yangmin
Szostak, Michal
ORGANIC LETTERS, 2020, 22 (13) : 5187 - 5192
[42] Synthesis of optically active partly gem-difluorinated allylic alcohols via [2,3]-Wittig rearrangements and lipase-catalyzed reaction
Itoh, T
Kudo, K
Tanaka, N
Sakabe, K
Takagi, Y
Kihara, H
TETRAHEDRON LETTERS, 2000, 41 (23) : 4591 - 4595
[43] Synthesis of Stereodefined 3-Alkylideneoxindoles by Palladium-catalyzed Reactions of 2-(Alkynyl)aryl Isocyanates with Thiols and Alcohols
Miura, Tomoya
Toyoshima, Takeharu
Ito, Yoshiteru
Murakami, Masahiro
CHEMISTRY LETTERS, 2009, 38 (12) : 1174 - 1175
[44] Organocascade Synthesis of Bicyclo[3.3.1] nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones
Wang, De-Chih
Huang, Pin-Han
Huang, Wan-Wun
Cheng, You-Song
Chen, Kwunmin
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) : 3005 - 3013
[45] Synthesis of 2-(1-Aryl-2-nitroethyl)-3-arylaminoacrylates via Domino Reaction of Arylamines, Methyl Propiolate, and Nitrostyrenes
Sun, Jing
Sun, Yan
Gao, Hong
Yan, Chao-Guo
SYNTHESIS-STUTTGART, 2012, 44 (07): : 1069 - 1073
[46] PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .1. NEW SYNTHESIS OF 2-PHENYL AND 3-PHENYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ALLYLIC ALCOHOLS
CHALK, AJ
MAGENNIS, SA
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02): : 273 - 278
[47] Asymmetric Synthesis of Spirocyclopentane Oxindoles via [2+3] Annulation with 2-(2-Oxoindolin-3-yl)malononitriles as 1,2-Carbon Bisnucleophiles
Ai, Yue-Yan
Li, Dong-Ai
Li, Guo
Li, He-Ping
He, Xiang-Hong
Fu, Xue-Ju
Wang, Yu-Ting
Zhan, Gu
Han, Bo
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (13) : 3283 - 3289
[48] Cu(II)/Ag(I)-Catalyzed Cascade Reaction of Sulfonylhydrazone with Anthranils: Synthesis of 2-Aryl-3-sulfonyl Substituted Quinoline Derivatives
Wang, Fei
Xu, Pei
Wang, Shun-Yi
Ji, Shun-Jun
ORGANIC LETTERS, 2018, 20 (08) : 2204 - 2207
[49] Synthesis of 2-(diarylmethylene)-3-benzofuranones promoted via palladium-catalyzed reactions of aryl iodides with 3-aryl-1-(2-tert-butyldimethylsilyloxy)phenyl-2-propyn-1-ones
Lin, CF
Lu, WD
Wang, IW
Wu, MJ
SYNLETT, 2003, (13) : 2057 - 2061
[50] Organocatalytic asymmetric Friedel-Crafts reaction of 1-naphthols with isatins: an enantioselective synthesis of 3-aryl-3-hydroxy-2-oxindoles
Kaur, Jasneet
Kumar, Akshay
Chimni, Swapandeep Singh
TETRAHEDRON LETTERS, 2014, 55 (13) : 2138 - 2141

← 1 2 3 4 5 →