Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

被引：27

作者：

Edeson, Steven J. ^{[1
]}

Jiang, Julong ^{[1
]}

Swanson, Stephen ^{[2
]}

Procopiou, Panayiotis A. ^{[2
]}

Adams, Harry ^{[1
]}

Meijer, Anthony J. H. M. ^{[1
]}

Harrity, Joseph P. A. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

ELUCIDATION; COMPLEXES; ACID; DFT;

D O I：

10.1039/c4ob00496e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

引用

页码：3201 / 3210

页数：10

共 16 条

[1] Isolation and Structure Elucidation of Satosporin A and B: New Polyketides from Kitasatospora griseola [J].

Arens, Jennifer C. ;

Berrue, Fabrice ;

Pearson, Jason K. ;

Kerr, Russell G. .

ORGANIC LETTERS, 2013, 15 (15) :3864-3867

[2] Structure and intramolecular stabilization of geometric isomers of Bi- and trithiazolidine-4-ones and their methyl derivatives: A DFT and QTAIM study [J].

Baryshnikov, G. V. ;

Minaev, B. F. ;

Minaeva, V. A. ;

Baryshnikova, A. T. .

JOURNAL OF STRUCTURAL CHEMISTRY, 2012, 53 (03) :428-435

[3] Quantum-chemical study of structure and spectral properties of triphenylamine-rhodanine dye 2-(5-(4-(diphenylamine)benzylidene)-4-oxo-2-thioxothiazolidine-3-yl) acetic acid [J].

Baryshnikov, G. V. ;

Minaev, B. F. ;

Minaeva, V. A. .

OPTICS AND SPECTROSCOPY, 2011, 110 (02) :216-223

[4] Theoretical study of the conformational structure and thermodynamic properties of 5-(4-oxo-1,3-thiazolidine-2-ylidene)-rhodanine and ethyl-5-(4-oxo-1,3-thiazolidine-2-ylidene)-rhodanine-3-acetic acid as acceptor groups of indoline dyes [J].

Baryshnikov, G. V. ;

Minaev, B. F. ;

Minaeva, V. A. ;

Agren, H. .

JOURNAL OF STRUCTURAL CHEMISTRY, 2010, 51 (05) :817-823

[5] Condensations of isatm with acetone by the Knoevenagel method [J].

Braude, F ;

Lindwall, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :325-327

[6] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[7]

Faita G., 1994, TETRAHEDRON, V37, P10955

[8] Acylideneoxoindoles: A new class of reversible inhibitors of human transglutaminase 2 [J].

Kloeck, Cornelius ;

Jin, Xi ;

Choi, Kihang ;

Khosla, Chaitan ;

Madrid, Peter B. ;

Spencer, Andrew ;

Raimundo, Brian C. ;

Boardman, Paul ;

Lanza, Guido ;

Griffin, John H. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (09) :2692-2696

[9]

Le Tourneau Christophe, 2007, Ther Clin Risk Manag, V3, P341, DOI 10.2147/tcrm.2007.3.2.341

[10] 3-Alkenyl-oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/Telescoped Approaches [J].

Millemaggi, Alessia ;

Taylor, Richard J. K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (24) :4527-4547

← 1 2 →