Stereoselective synthesis of (E)-4-(imidazo[1,2-a]pyrid-2-yl)-3-(4-methylphenylsulfonyl)but-3-en-2-one. X-ray crystal structure and conformational analysis

被引：1

作者：

Roche, D

Force, L

Carpy, A

Gardette, D

Madesclaire, M

机构：

[1] Univ Auvergne, UFR Pharm, Dept Anal Struct & Pharmacologie, F-63001 Clermont Ferrand, France

[2] Univ Bordeaux 1, Lab Physico & Toxicochim Syst Nat, UPRES A 5472, F-33405 Talence, France

[3] Univ Blaise Pascal, F-63177 Clermont Ferrand, France

来源：

JOURNAL OF MOLECULAR STRUCTURE | 1998年 / 447卷 / 1-2期

关键词：

stereoselective synthesis; X-ray crystal structure; conformational analysis;

D O I：

10.1016/S0022-2860(98)00316-0

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The title compound, gem-ketovinylsulfone 3, was obtained stereoselectively (de > 98%) by the action of the oc-anion from p-tolylsulfonylacetone 1 on imidazo[1,2-a]pyridine-2-carbaldehyde 2 in chelation-controlled conditions in the presence of a Lewis acid (ZnCl2). The X-ray crystal structure of 3 [C18H16N2O3S: M-I = 340.4, orthorhombic, Pbca, a = 12.208(3) Angstrom, b = 18.848(4)Angstrom, c = 14.566(11)Angstrom, V = 3.351(3)Angstrom(3), Z = 8, D-calc = 1.349 g cm(-3), <(lambda)over bar>(CuK alpha) = 1.54178 Angstrom, mu = 1.83 mm(-1), F(000) = 1424, T = 293 K, R = 0.061 for 2.046 observed reflections] was determined, and confirmed the (E) configuration. Despite the conjugate position of the vinyl double bond, quasi-coplanar with the imidazopyridine heterocycle, there is no evidence of p-electron delocalization. The crystal cohesion is ensured by a dense network of van der Waals contacts. The conformational analysis of the (E) and (Z) stereoisomers was performed by molecular dynamics simulation, and showed the (E) isomer to be 9.1 kJ mol(-1) more stable than the (Z) isomer. (C) 1998 Elsevier Science B.V. All rights reserved.

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页码：135 / 140

页数：6

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