3-芳基-5-(芳基烷基)-6-甲基-1-(1-苯乙基)硫代四氢嘧啶-4(1H)-酮的非对映选择性合成：内型和外型手性中心的立体化学观点。

Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: a stereochemical perspective from endo and exocyclic chiral centres.

机构信息

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, Mohali, Punjab 160 062, India.

出版信息

Org Biomol Chem. 2010 Nov 7;8(21):4960-70. doi: 10.1039/c0ob00230e. Epub 2010 Sep 2.

DOI:10.1039/c0ob00230e

PMID:20820657

Abstract

Diastereoselective syntheses of 3-aryl-(S/R)-6-methyl-1-[(S/R)-1-phenylethyl)]-2-thioxotetrahydro pyrimidin-4(1H)-ones were achieved in good yields by the condensation of aryl isothiocyanates with ethyl 3-(1-phenylethylamino)butanoate in a one-pot reaction. Benzylation of these substrates illustrated that the orientations of the exocylic and endocylic groups determine the stereochemical outcome of the product formed.

摘要

通过芳基异硫氰酸酯与乙基 3-(1-苯乙基氨基)丁酸酯在一锅反应中的缩合反应，以良好的收率实现了 3-芳基-(S/R)-6-甲基-1-[(S/R)-1-苯乙基)]-2-硫代四氢嘧啶-4(1H)-酮的对映选择性合成。这些底物的苄基化表明，外消旋和内消旋基团的取向决定了形成的产物的立体化学结果。