SO2ClF-Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3-Disubstituted Oxindoles

被引：1

作者：

Zheng, Yu ^{[1
]}

Lu, Wenguang ^{[1
]}

Ma, Tianting ^{[1
]}

Huang, Shenlin ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat, Forest Resources Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 01期

基金：

中国国家自然科学基金;

关键词：

3-chlorooxindoles; tryptamine derivatives; chlorooxidation; 3,3-disubstituted oxindoles; gram-scale reaction; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE BROMOCYCLIZATION; 3-BROMOOXINDOLES; CONSTRUCTION; ALKYLATION; 3-CHLOROOXINDOLES; TRANSFORMATION; CHLORINATION; ANNULATION; CHLORIDE;

D O I：

10.1002/ajoc.202300552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of tryptamine derivatives were transformed into their corresponding 3-chloro-2-oxidation products under simple and mild conditions. This protocol is an operationally simple system that utilizes a single reagent SO2ClF plays a dual role as both oxidant and chloride source and enables the construction of various 3,3-disubstituted oxindoles with good functional group tolerance. The transformations of the product highlight its potential synthetic applications.

引用

页数：5

共 65 条

[41] Asymmetric Synthesis of α-Fluoro-β-Amino-oxindoles with Tetrasubstituted C-F Stereogenic Centers via Cooperative Cation Binding Catalysis [J].

Paladhi, Sushovan ;

Park, Sang Yeon ;

Yang, Jung Woon ;

Song, Choong Eui .

ORGANIC LETTERS, 2017, 19 (19) :5336-5339

[42] Synthesis, molecular docking, and QSAR study of sulfonamide-based indoles as aromatase inhibitors [J].

Pingaew, Ratchanok ;

Mandi, Prasit ;

Prachayasittikul, Veda ;

Prachayasittikul, Supaluk ;

Ruchirawat, Somsak ;

Prachayasittikul, Virapong .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :1604-1615

[43] Base-promoted ring opening of 3-chlorooxindoles for the construction of 2-aminoarylthioates and their transformation to quinazolin-4(3H)-ones [J].

Poudel, Tej Narayan ;

Khanal, Hari Datta ;

Lee, Yong Rok .

NEW JOURNAL OF CHEMISTRY, 2018, 42 (06) :4735-4741

[44] An efficient synthesis of versatile synthon 3-chlorooxindoles with NaCl/oxone [J].

Reddy, Vanammoole Lakshmi ;

Prathima, Parvathaneni Sai ;

Rao, Vaidya Jayathirtha ;

Bikshapathi, Raktani .

NEW JOURNAL OF CHEMISTRY, 2018, 42 (24) :20152-20155

[45]

REDDY VP, 1992, J FLUORINE CHEM, V56, P195

[46] Construction of Peptide-Isoquinolone Conjugates via Rh(III)- Catalyzed C-H Activation/Annulation [J].

Song, Liangliang ;

Lv, Zhenwei ;

Li, Yan ;

Zhang, Kui ;

Van der Eycken, Erik V. ;

Cai, Lingchao .

ORGANIC LETTERS, 2023, 25 (17) :2996-3000

[47] Catalytic Asymmetric Synthesis of Pyrroloindolines via a Rhodium(II)-Catalyzed Annulation of Indoles [J].

Spangler, Jillian E. ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (18) :6802-6805

[48] Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline [J].

Thomson, Jennifer E. ;

Kyle, Andrew F. ;

Ling, Kenneth B. ;

Smith, Siobhan R. ;

Slawin, Alexandra M. Z. ;

Smith, Andrew D. .

TETRAHEDRON, 2010, 66 (21) :3801-3813

[49] Synthesis of Pyrrolo[2,3-b]indole via Iodine(III)-Mediated Intramolecular Annulation [J].

Tu, Dandan ;

Ma, Liying ;

Tong, Xiaogang ;

Deng, Xu ;

Xia, Chengfeng .

ORGANIC LETTERS, 2012, 14 (18) :4830-4833

[50] Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone [J].

Uyanik, Muhammet ;

Sahara, Naoto ;

Ishihara, Kazuaki .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (01) :27-31

← 1 2 3 4 5 6 7 →