Four-Component Regio- and Diastereoselective Synthesis of Pyrrolizidines Incorporating Spiro-Oxindole/Indanedione via 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides

被引：18

作者：

Alizadeh, Abdolali ^{[1
]}

Roosta, Atefeh ^{[1
]}

Halvagar, Mohammadreza ^{[2
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran

[2] Chem & Chem Engn Res Ctr Iran, Pajohesh Blvd,17th Km Tehran Karaj Highway, Tehran 1496813151, Iran

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 01期

关键词：

azomethine ylides; 2-chloroquinoline-3-carbaldehyde; diastereoselective; four-component 1,3-dipolar cycloaddition reaction; isatin; L-proline; ninhydrine; 4-oxo-4H-chromene-3-carbaldehyde; 1-phenyl-2-(1,1,1-triphenyl-lambda(5)-phosphanylidene)ethan-1-one; regioselective; spiro-indanedionepyrrolizidine; spiro-oxindolopyrrolizidine; STRUCTURE-BASED DESIGN; ONE-POT; QUINOLINE; SPIROOXINDOLES; QUINAZOLINE; INHIBITORS; EFFICIENT;

D O I：

10.1002/slct.201803418

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The present investigation reports an easy regio- and diastereoselective access to a library of diverse polycyclic pyrrolizidine fused spiro-1,3-indandione/oxindole derivatives through a one-pot sequential four-component reactions of 4-oxo-4H-chromene-3-carbaldehyde/2-chloroquinoline-3-carbaldehyde, 1-phenyl-2-(1,1,1-triphenyl-lambda(5)-phosphanylidene)ethan-1-one, ninhydrin or isatin, and L-proline in EtOH at room temperature. This protocol features excellent chemical yields, high diastereoselectivity and operational simplicity.

引用

收藏

页码：71 / 74

页数：4

相关论文

共 45 条

[1] Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2014, 50 (83) :12434-12446

[2] Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1351-1358

[3] Efficient one pot and chemoselective synthesis of functionalized 3-bromo-4,5-dihydroisoxazole derivatives &ITvia &IT1,3-dipolar cycloaddition reactions of nitrile oxides [J].

Alizadeh, Abdolali ;

Roosta, Atefeh ;

Rezaiyehrad, Reza ;

Halvagar, Mohammadreza .

TETRAHEDRON, 2017, 73 (48) :6706-6711

[4] A Convenient Approach for the Synthesis of 1,3-Diphenyl-1H-pyrazole-5-carbonitrile [J].

Alizadeh, Abdolali ;

Roosta, Atefeh .

SYNLETT, 2016, 27 (17) :2455-2458

[5]

[Anonymous], 2017, APPL ORGANOMET CHEM

[6] Synthesis and antibacterial evaluation of certain quinolone derivatives [J].

Chen, YL ;

Fang, KC ;

Sheu, JY ;

Hsu, SL ;

Tzeng, CC .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377

[7] Asymmetric [3+2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3′-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters [J].

Chen, Yu ;

Cui, Bao-Dong ;

Wang, Yi ;

Han, Wen-Yong ;

Wan, Nan-Wei ;

Bai, Mei ;

Yuan, Wei-Cheng ;

Chen, Yong-Zheng .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17) :10465-10475

[8]

Cui BD, 2017, ORG BIOMOL CHEM, V15, P8518, DOI [10.1039/c7ob02138krsc.li/obc, 10.1039/c7ob02138k]

[9] Synthesis of 2,3'-spirobi[indolin]-2-ones enabled by a tandem nucleophilic benzylation/C(sp2)- N cross-coupling reaction sequence [J].

Cui, Baodong ;

Shan, Jing ;

Yuan, Changlun ;

Han, Wenyong ;

Wan, Nanwei ;

Chen, Yongzheng .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (28) :5887-5892

[10] Comparative Study of the Affinity and Metabolism of Type I and Type II Binding Quinoline Carboxamide Analogues by Cytochrome P450 3A4 [J].

Dahal, Upendra P. ;

Joswig-Jones, Carolyn ;

Jones, Jeffrey P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (01) :280-290

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