A rapid and high efficient microwave promoted multicomponent domino reaction for the synthesis of spirooxindole derivatives

被引：14

作者：

Ghahremanzadeh, Ramin ^{[1
]}

Rashid, Zahra ^{[2
]}

Zarnani, Amir-Hassan ^{[3
]}

Naeimi, Hossein ^{[2
]}

机构：

[1] ACECR, Avicenna Res Inst, Nanobiotechnol Res Ctr, Tehran, Iran

[2] Univ Kashan, Fac Chem, Dept Organ Chem, Kashan 87317, Iran

[3] ACECR, Avicenna Res Inst, Reprod Immunol Res Ctr, Tehran, Iran

来源：

JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY | 2014年 / 20卷 / 06期

关键词：

Multi-component reaction; Alum [KAl(SO4)(2)center dot 12H(2)O; Microwave; Anilinolactone; Spirooxindole; ONE-POT SYNTHESIS; FACILE SYNTHESIS; INDOLE; INHIBITOR; CATALYST; WATER;

D O I：

10.1016/j.jiec.2013.12.109

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple, efficient and rapid method has been developed for synthesis of 6,6-dimethyl-4-phenyl-6,7-dihydro-1H-spiro[furo[3,4-b]quinoline-9,3'-indoline]1,2',8(3H,4H,5H)-trione derivatives. These heterocycles were prepared through domino one-pot and multicomponent condensation reactions of isatins, dimedone, and anilinolactones in the presence of alum (15 mol%) as an inexpensive, nontoxic, convenient, and available Lewis acid catalyst under microwave irradiation. The corresponding products have been obtained in excellent isolated yields between 78% and 90%, with high purity, in short reaction times about 10-12 min and easy work up. (C) 2014 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.

引用

页码：4076 / 4084

页数：9

共 41 条

[1] Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].

Abdel-Rahman, AH ;

Keshk, EM ;

Hanna, MA ;

El-Bady, SM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488

[2] Synthesis of spiro[benzopyrazolonaphthyridine-indoline]-diones and spiro[chromenopyrazolopyridine-indoline]-diones by one-pot, three-component methods in water [J].

Ahadi, Somayeh ;

Ghahremanzadeh, Ramin ;

Mirzaei, Peiman ;

Bazgir, Ayoob .

TETRAHEDRON, 2009, 65 (45) :9316-9321

[3] Synthesis of Heterocyclic [3.3.3]Propellanes via a Sequential Four-Component Reaction [J].

Alizadeh, Abdolali ;

Rezvanian, Atieh ;

Zhu, Long-Guan .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) :4385-4390

[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] Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine [J].

Baeza, A ;

Nájera, C ;

Retamosa, MD ;

Sansano, JM .

SYNTHESIS-STUTTGART, 2005, (16) :2787-2797

[6] One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by Lipase in the Presence of Water [J].

Chai, She-Jie ;

Lai, Yi-Feng ;

Xu, Jiang-Cheng ;

Zheng, Hui ;

Zhu, Qing ;

Zhang, Peng-Fei .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :371-375

[7] Synthesis of C-homoaporphines via microwave-assisted direct arylation [J].

Chaudhary, Sandeep ;

Harding, Wayne W. .

TETRAHEDRON, 2011, 67 (03) :569-575

[8] Efficient One-Pot Synthesis of Novell Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium [J].

Chen, Hui ;

Shi, Daqing .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04) :571-576

[9] [4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives [J].

Cheng, Chuang ;

Jiang, Bo ;

Tu, Shu-Jiang ;

Li, Guigen .

GREEN CHEMISTRY, 2011, 13 (08) :2107-2115

[10] Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835

← 1 2 3 4 5 →