Molecular Iodine-Mediated Ring Opening Reaction of Spiro-Epoxy Oxindoles with Electron Rich Arenes

被引：4

作者：

Shanker, Medi ^{[1
]}

Venkanna, Avudoddi ^{[1
]}

Prasad, Pulaganti Vijaya ^{[1
]}

Swamy, Marapala Kumara ^{[1
]}

Rao, Pallapothula Venkateswar ^{[1
]}

机构：

[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 31期

关键词：

Electron rich arenes; Friedel-Crafts reaction; Molecular iodine; Spiro-epoxy; 2-oxindoles; 3,3-diSubstituted 2-oxindoles; GROWTH-HORMONE SECRETAGOGUES; TRANSLATION INITIATION; DERIVATIVES; ALKALOIDS; EPOXYOXINDOLES; HETEROCYCLES; DESIGN;

D O I：

10.1002/slct.201701561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly efficient and facile methodology has been developed for the ring opening reaction of spiro-epoxy oxindoles with electron rich arenes in presence of molecular iodine. These reactions can be carried out easily under mild reaction conditions to afford functionalized 2-indolinone derivatives in excellent yields.

引用

页码：10150 / 10152

页数：3

共 38 条

[1] Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes [J].

Aggarwal, Trapti ;

Kumar, Sonu ;

Verma, Akhilesh K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (32) :7639-7653

[2] Palladium-catalyzed highly atom-economical allylation of oxindoles with vinyl cyclopropanes [J].

Cao, Ruwei ;

Zhang, Jinlong ;

Zhou, Hui ;

Yang, Huameng ;

Jiang, Gaoxi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (07) :2191-2194

[3] Synthesis and Antitumor Effect in Vitro and in Vivo of Substituted 1,3-Dihydroindole-2-ones [J].

Christensen, Mette K. ;

Erichsen, Kamille D. ;

Trojel-Hansen, Christina ;

Tjornelund, Jette ;

Nielsen, Soren J. ;

Frydenvang, Karla ;

Johansen, Tommy N. ;

Nielsen, Birgitte ;

Schested, Maxwell ;

Jensen, Peter B. ;

Ikaunieks, Martins ;

Zaichenko, Andrei ;

Loza, Einars ;

Kalvinsh, Ivars ;

Bjorkling, Fredrik .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7140-7145

[4] Iodine, a Mild Reagent for the Aromatization of Terpenoids [J].

Domingo, Victoriano ;

Prieto, Consuelo ;

Silva, Lucia ;

Rodilla, Jesus M. L. ;

Quilez del Moral, Jose F. ;

Barrero, Alejandro F. .

JOURNAL OF NATURAL PRODUCTS, 2016, 79 (04) :831-837

[5] Identification of the Spiro(oxindole-3,3′-thiazolidine)-Based Derivatives as Potential p53 Activity Modulators [J].

Gomez-Monterrey, Isabel ;

Bertamino, Alessia ;

Porta, Amalia ;

Carotenuto, Alfonso ;

Musella, Simona ;

Aquino, Claudio ;

Granata, Ilaria ;

Sala, Marina ;

Brancaccio, Diego ;

Picone, Delia ;

Ercole, Carmine ;

Stiuso, Paola ;

Campiglia, Pietro ;

Grieco, Paolo ;

Ianelli, Pio ;

Maresca, Bruno ;

Novellino, Ettore .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (23) :8319-8329

[6] Regioselective Friedel-Crafts Reaction of Electron-Rich Benzenoid Arenes and Spiroepoxyoxindole at the Spiro-Centre: Efficient Synthesis of Benzofuroindolines and 2H-Spiro[benzofuran]-3,3′-oxindoles [J].

Hajra, Saumen ;

Maity, Subrata ;

Roy, Sayan .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (14) :2300-2306

[7] Efficient Synthesis of 3,3′-Mixed Bisindoles via Lewis Acid Catalyzed Reaction of Spiro-epoxyoxindoles and Indoles [J].

Hajra, Saumen ;

Maity, Subrata ;

Maity, Ramkrishna .

ORGANIC LETTERS, 2015, 17 (14) :3430-3433

[8] Iodine-Catalyzed Direct Olefination of 2-Oxindoles and Alkenes via Cross-Dehydrogenative Coupling (CDC) in Air [J].

Huang, Hong-Yan ;

Wu, Hong-Ru ;

Wei, Feng ;

Wang, Dong ;

Liu, Li .

ORGANIC LETTERS, 2015, 17 (15) :3702-3705

[9] When gold can do what iodine cannot do: A critical comparison [J].

Hummel, Sara ;

Kirsch, Stefan F. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :847-859

[10] Facile and diastereoselective synthesis of 3,2′-spiropyrrolidine-oxindoles derivatives, their molecular docking and antiproliferative activities [J].

Kathirvelan, D. ;

Haribabu, J. ;

Reddy, B. S. R. ;

Balachandran, C. ;

Duraipandiyan, V. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (02) :389-399

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