Non-biaryl atropisomers derived from carbohydrates.: Part 1.: Stereoselective synthesis of 1-aryl-5-hydroxyimidazolidine-2-thiones and their transformation into imidazoline-2-thiones

被引：17

作者：

Avalos, M ^{[1
]}

Babiano, R ^{[1
]}

Cintas, P ^{[1
]}

Jiménez, JL ^{[1
]}

Palacios, JC ^{[1
]}

Silvero, G ^{[1
]}

Valencia, C ^{[1
]}

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 14期

关键词：

atropisomerism; carbohydrates; imidazolidine-2-thiones; imidazoline-2-thiones; NMR spectroscopy;

D O I：

10.1016/S0040-4020(99)00109-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of chiral 5-hydroxyimidazolidine-2-thiones bearing an ortho-substituted aromatic residue at N-1, which are readily accessible from D-glucosamine, have been synthesized as potential atropisomers. In general, these substances display a trans arrangement between H-4 and H-5, and hence the absolute configuration at C-5 was shown to be R. However the first example of this type of structures having a cis configuration (S at C-5) is also described. Moreover, the mechanistic features associated with the conversion of 5-acetoxyimidazolidine-2-thiones into imidazoline-2-thiones have also been evaluated. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4377 / 4400

页数：24

共 43 条

[1] CARBOHYDRATE-DERIVED MESIONIC COMPOUNDS .1. SYNTHESIS AND REACTIVITY TOWARD ACETYLENIC DIPOLAROPHILES OF IMIDAZO(2,1-B)THIAZOLIUM-3-OLATE SYSTEMS [J].

ARECES, P ;

AVALOS, M ;

BABIANO, R ;

GONZALEZ, L ;

JIMENEZ, JL ;

PALACIOS, JC ;

PILO, MD .

CARBOHYDRATE RESEARCH, 1991, 222 :99-112

[2] ON THE MECHANISM OF FORMATION OF GLYCOFURANO[2,1-D]-IMIDAZOLIDIN-2-ONES - REACTION OF 2-AMINO-2-DEOXYHEPTOPYRANOSES WITH ISOCYANATES [J].

AVALOS, M ;

BABIANO, R ;

CINTAS, P ;

JIMENEZ, JL ;

PALACIOS, JC ;

VALENCIA, C .

TETRAHEDRON, 1993, 49 (13) :2676-2690

[3] CONDENSATION OF 2-AMINO-2-DEOXYSUGARS WITH ISOTHIOCYANATES - SYNTHESIS OF CIS-1,2-FUSED GLYCOPYRANO HETEROCYCLES [J].

AVALOS, M ;

BABIANO, R ;

CINTAS, P ;

JIMENEZ, JL ;

PALACIOS, JC ;

VALENCIA, C .

TETRAHEDRON, 1994, 50 (10) :3273-3296

[4] THE REACTION OF 2-AMINO-2-DEOXYHEXOPYRANOSES WITH ISOCYANATES, SYNTHESIS OF UREAS AND THEIR TRANSFORMATION INTO HETEROCYCLIC-DERIVATIVES [J].

AVALOS, M ;

BABIANO, R ;

CINTAS, P ;

JIMENEZ, JL ;

PALACIOS, JC ;

VALENCIA, C .

TETRAHEDRON, 1993, 49 (13) :2655-2675

[5]

AVALOS M, 1986, CARBOHYD RES, V158, P53

[6] CONFORMATION OF ACYCLIC DERIVATIVES OF SUGARS .15. CONFORMATIONS IN SOLUTION OF THE STEREOISOMERIC, PERACETYLATED ALDOHEXOSE DIMETHYL ACETALS AND DIETHYL DITHIOACETALS [J].

BLANCMUESSER, M ;

DEFAYE, J ;

HORTON, D .

CARBOHYDRATE RESEARCH, 1980, 87 (01) :71-86

[7]

BOCK K, 1983, ADV CARBOHYD CHEM BI, V41, P54

[8]

Bock L.H., 1931, J Am Chem Soc, V53, P374

[9] Stereochemistry of phenyl pyrroles. XIX [J].

Bock, LH ;

Adams, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1931, 53 :3519-3522

[10]

COXON B, 1972, METHODS CARBOHYD CHE, V6, P513

← 1 2 3 4 5 →