Efficient construction of diverse spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via [3+3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides

被引：24

作者：

Pan, Liu-Na ^{[1
]}

Sun, Jing ^{[1
]}

Liu, Xue-Yan ^{[1
]}

Yan, Chao-Guo ^{[1
]}

机构：

[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 35期

基金：

中国国家自然科学基金;

关键词：

POT MULTICOMPONENT SYNTHESIS; BAYLIS-HILLMAN CARBONATES; STEREOSELECTIVE-SYNTHESIS; CONVENIENT SYNTHESIS; 4-COMPONENT REACTION; SPIROOXINDOLES; ANTICANCER; FACILE; SPIRO; DERIVATIVES;

D O I：

10.1039/d2ob01257j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method to construct unique spiro[indoline-3,4 '-pyrrolo[3,4-b]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates of isatins with beta-enamino maleimides in acetonitrile at room temperature. This reaction afforded multifunctionalized spiro[indoline-3,4 '-pyrrolo[3,4-b]pyridines] and spiro[dipyrrolo[3,4-b:3 ',4 '-e]pyridine-8,3 '-indolines] in good yields and with lower diastereoselectivity. The relative configuration of the two diasteromers of the spiro compounds was clearly elucidated by the determination of eight single crystal structures.

引用

页码：7099 / 7104

页数：6

共 68 条

[1] An Efficient Synthesis of Spiro-oxindole Derivatives by Three-Component Reactions in Water [J].

Alizadeh, Abdolali ;

Moafi, Leila .

HELVETICA CHIMICA ACTA, 2015, 98 (04) :546-551

[2] Novel four-component route to the synthesis of spiro[indoline-3,4′-pyridine]-3′-carboxylate derivatives [J].

Alizadeh, Abdolali ;

Mokhtari, Javad .

TETRAHEDRON, 2011, 67 (19) :3519-3523

[3] Cyanoacetanilide intermediates in heterocyclic synthesis. Part 7: preparation of some spiro[indoline-3,4′-pyridine] and chromeno[3,4-c]pyridine derivatives [J].

Ammar, Yossry A. ;

Ali, Mohsan M. ;

Mohamed, Yahia A. ;

Thabet, Hamdy Khamees ;

El-Gaby, Mohamed S. A. .

HETEROCYCLIC COMMUNICATIONS, 2013, 19 (03) :195-200

[4] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].

Antonchick, Andrey P. ;

Gerding-Reimers, Claas ;

Catarinella, Mario ;

Schuermann, Markus ;

Preut, Hans ;

Ziegler, Slava ;

Rauh, Daniel ;

Waldmann, Herbert .

NATURE CHEMISTRY, 2010, 2 (09) :735-740

[5] Novel spirooxindole-pyrrolidine compounds: Synthesis, anticancer and molecular docking studies [J].

Arun, Y. ;

Saranraj, K. ;

Balachandran, C. ;

Perumal, P. T. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 74 :50-64

[6] Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line [J].

Arun, Y. ;

Bhaskar, G. ;

Balachandran, C. ;

Ignacimuthu, S. ;

Perumal, P. T. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (06) :1839-1845

[7] Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita-Baylis-Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO [J].

Arupula, Sanjeeva K. ;

Guin, Soumitra ;

Yadav, Anubha ;

Mobin, Shaikh M. ;

Samanta, Sampak .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) :2660-2675

[8] A domino protocol for the efficient synthesis of structurally diverse benzothiazolylquinoline-2,5-diones and their spiro analogues [J].

Arya, Anand Kumar ;

Gupta, Sunil Kumar ;

Kumar, Mahendra .

TETRAHEDRON LETTERS, 2012, 53 (45) :6035-6038

[9] Baylis-Hillman carbonates in organic synthesis: a convenient one-pot strategy for nitrone-spiro-oxindole frameworks [J].

Basavaiah, Deevi ;

Badsara, Satpal Singh ;

Veeraraghavaiah, Gorre .

TETRAHEDRON, 2013, 69 (37) :7995-8001

[10] Baylis-Hillman Bromides as a Source of 1,3-Dipoles: Sterically Directed Synthesis of Oxindole-Fused Spirooxirane and Spirodihydrofuran Frameworks [J].

Basavaiah, Deevi ;

Badsara, Satpal Singh ;

Sahu, Bharat Chandra .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (09) :2961-2965

← 1 2 3 4 5 6 7 →