Thiazolidinedione-Isatin Conjugates via an Uncatalyzed Diastereoselective Aldol Reaction on Water

被引：46

作者：

Paladhi, Sushovan ^{[1
,2
]}

Bhati, Meeta ^{[2
]}

Panda, Deepanjan ^{[1
]}

Dash, Jyotirmayee ^{[1
,2
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

[2] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741252, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 03期

关键词：

ORGANIC-SYNTHESIS; SOLVENT-FREE; IN-WATER; CATALYSIS; CHEMISTRY; EFFICIENT; PYRROLE;

D O I：

10.1021/jo402515d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An uncatalyzed aldol reaction of N-substituted thiazolidinediones with isatin derivatives has been developed "on water" to afford a new class of pharmacologically important thiazolidinedione-isatin conjugates in excellent yields and diastereoselectivities. The isatin-thiazolidine conjugate undergoes a catalyst-free stereoselective transfer aldol reaction on water. Single-crystal X-ray studies reveal that the aldol products can self-assemble to form supramolecular DNA "zipper" like structures through intermolecular hydrogen bonds and aromatic pi-pi interactions.

引用

页码：1473 / 1480

页数：8

共 49 条

[1] Claisen Rearrangements: Insight into Solvent Effects and "on Water" Reactivity from QM/MM Simulations [J].

Acevedo, Orlando ;

Armacost, Kira .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1966-1975

[2]

Anastas PT., 1998, GREEN CHEM FRONTIERS, DOI DOI 10.1021/JA995756G

[3] Synthesis, in Vitro, and in Cell Studies of a New Series of [Indoline-3,2′-thiazolidine]-Based p53 Modulators [J].

Bertamino, Alessia ;

Soprano, Maria ;

Musella, Simona ;

Rusciano, Maria Rosaria ;

Sala, Marina ;

Vernieri, Errnelinda ;

Di Sarno, Veronica ;

Limatola, Antonio ;

Carotenuto, Alfonso ;

Cosconati, Sandro ;

Grieco, Paolo ;

Novellino, Ettore ;

Illario, Maddalena ;

Campiglia, Pietro ;

Gomez-Monterrey, Isabel .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (13) :5407-5421

[4] Water and Organic Synthesis: A Focus on the In-Water and On-Water Border. Reversal of the In-Water Breslow Hydrophobic Enhancement of the Normal endo-Effect on Crossing to On-Water Conditions for Huisgen Cycloadditions with Increasingly Insoluble Organic Liquid and Solid 2π-Dipolarophiles [J].

Butler, Richard N. ;

Coyne, Anthony G. ;

Cunningham, William J. ;

Moloney, Eamon M. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3276-3291

[5] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

[6] Organic Synthesis "On Water" [J].

Chanda, Arani ;

Fokin, Valery V. .

CHEMICAL REVIEWS, 2009, 109 (02) :725-748

[7] Lewis base-catalyzed three-component Strecker reaction on water. An efficient manifold for the direct α-cyanoamination of ketones and aldehydes [J].

Cruz-Acosta, Fabio ;

Santos-Exposito, Alicia ;

de Armas, Pedro ;

Garcia-Tellado, Fernando .

CHEMICAL COMMUNICATIONS, 2009, (44) :6839-6841

[8] Uncatalyzed, Diastereoselective Vinylogous Mukaiyama Aldol Reactions on Aqueous Media: Pyrrole vs Furan 2-Silyloxy Dienes [J].

Curti, Claudio ;

Battistini, Lucia ;

Zanardi, Franca ;

Rassu, Gloria ;

Zambrano, Vincenzo ;

Pinna, Luigi ;

Casiraghi, Giovanni .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8681-8684

[9] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[10] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

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