An Efficient One-Pot Synthesis of Dispiropyrrolidine Derivatives Through 1,3-Dipolar Cycloaddition Reactions Under Ultrasound Irradiation

被引：29

作者：

Liu, Hai ^{[1
]}

Zou, Yi ^{[2
]}

Hu, Yu ^{[1
]}

Shi, Da-Qing ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Xuzhou Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2011年 / 48卷 / 04期

关键词：

CLEAN SYNTHESIS; MULTICOMPONENT; IMINES;

D O I：

10.1002/jhet.654

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of dispiropyrrolidine derivatives were synthesized via the three-component 1,3-dipolar cycloaddition reaction of isatin, sarcosine and 5-arylidene-1,3-thiazolidine-2,4-dione or 5-arylidene-4-thioxo-1,3- thiazolidine-2-one in ethanol under ultrasound irradiation. This protocol has the advantages of mild reaction conditions, higher yields, and shorter reaction time.

引用

页码：877 / 881

页数：5

共 45 条

[1] Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents
Abdel-Rahman, AH
Keshk, EM
Hanna, MA
El-Bady, SM
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) : 2483 - 2488
[2] A concise asymmetric synthesis of the ADE fragment of nakadomarin
Ahrendt, KA
Williams, RM
[J]. ORGANIC LETTERS, 2004, 6 (24) : 4539 - 4541
[3] [Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
[4] [Anonymous], 1996, CHEM INDOLES
[5] A facile entry into a novel class of dispiroheterocyclic framework through 1,3-dipolarcycloaddition of azomethine ylides with 3-arylidene-4-chromanones as dipolarophiles
Augustine, T.
Kanakam, Charles C.
Vithiya, Scholastica Mary
Ramkumar, V.
[J]. TETRAHEDRON LETTERS, 2009, 50 (43) : 5906 - 5909
[6] Pd-assisted multicomponent synthesis of heterocycles
Balme, G
Bossharth, E
Monteiro, N
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) : 4101 - 4111
[7] Modulating the reactivity of α-isocyanoacetates:: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones
Bonne, Damien
Dekhane, Mouloud
Zhu, Jieping
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) : 2485 - 2488
[8] The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles
Bräse, S
Gil, C
Knepper, K
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) : 2415 - 2437
[9] Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones
Bruno, G
Costantino, L
Curinga, C
Maccari, R
Monforte, F
Nicolò, F
Ottanà, R
Vigorita, MG
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) : 1077 - 1084
[10] Intramolecular dipolar cycloaddition reactions of azomethine ylides
Coldham, I
Hufton, R
[J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809

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