2-(Benzoylimino)thiazolidin-4-ones: Formation by an Alternative Ring Closure and Analysis of Rotational Barriers

被引：9

作者：

Haecker, Hans-Georg ^{[1
]}

Elsinghorst, Paul W. ^{[1
]}

Michels, Susanne ^{[1
]}

Daniels, Joerg ^{[2
]}

Schnakenburg, Gregor ^{[2
]}

Guetschow, Michael ^{[1
]}

机构：

[1] Univ Bonn, Inst Pharmaceut, D-53121 Bonn, Germany

[2] Univ Bonn, Inst Inorgan Chem, D-53121 Bonn, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 07期

关键词：

atropisomerism; ring closure; regioselectivity; thiazolidin-4-ones; DFT calculations; REGIOSELECTIVE SYNTHESIS; DERIVATIVES; MOLECULES; CHEMISTRY; MICROWAVE; DESIGN; SULFUR; ACID;

D O I：

10.1055/s-0028-1087995

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of N-benzoyl-N'-(o-cyanoaryl)thioureas with ethyl bromoacetate under alkaline conditions led to the formation of either fused 2-(alkylsulfanyl)-4-aminopyrinlidines or 2(benzoylimino)-3-(o-cyanoatyl)thiazolidin-4-ones. The accurate application of slightly different reaction conditions allowed us to adjust the balance between the formation of the pyrimidine or thiazolidine heterocycles. Atropisomerism in the 3-(o-cyanoaryl)thiazolidin-4-ones was influenced by the size of the o-cyanoaryl ring, which was investigated by means of NMR measurements and theoretical calculations.

引用

页码：1195 / 1203

页数：9

共 39 条

[1] INFLUENCE OF AN ADJACENT SULPHUR ATOM ON GEMINAL COUPLING CONSTANTS IN METHYLENE GROUPS [J].

ALLINGHAM, Y ;

COOKSON, RC ;

CRABB, TA .

TETRAHEDRON, 1968, 24 (04) :1989-+

[2] BONDING BETWEEN NONBONDED SULFUR AND OXYGEN-ATOMS IN SELECTED ORGANIC-MOLECULES (A QUANTUM CHEMICAL STUDY) [J].

ANGYAN, JG ;

POIRIER, RA ;

KUCSMAN, A ;

CSIZMADIA, IG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2237-2245

[3]

[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014

[4] Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating [J].

Bolognese, A ;

Correale, G ;

Manfra, M ;

Lavecchia, A ;

Novellino, E ;

Barone, V .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) :2809-2813

[5]

Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661

[6]

BROUWER WG, 1986, Patent No. 200415

[7] An unexpected formation of 2-aryl-3-benzyl-1,3-thiazolidin-4-ones [J].

Cunico, Wilson ;

Capri, Liliane R. ;

Gomes, Claudia R. B. ;

Sizilio, Rosangela H. ;

Wardell, Solange M. S. V. .

SYNTHESIS-STUTTGART, 2006, 20 (20) :3405-3408

[8] SYNTHESIS AND ANTIHISTAMINIC ACTIVITY OF SOME THIAZOLIDIN-4-ONES [J].

DIURNO, MV ;

MAZZONI, O ;

PISCOPO, E ;

CALIGNANO, A ;

GIORDANO, F ;

BOLOGNESE, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (15) :2910-2912

[9] Axially chiral 2-arylimino-3-aryl-thiazolidine-4-one derivatives: Enantiomeric separation and determination of racemization barriers by chiral HPLC [J].

Erol, Sule ;

Dogan, Ilknur .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2494-2500

[10] New synthesis of substituted 4-amino-quinazolines and their heteroanalogs [J].

Gewald, K ;

Schafer, H ;

Eckert, K ;

Jeschke, T .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1996, 338 (03) :206-213

← 1 2 3 4 →