Stereoselective Knoevenagel reaction between pyrimidine carbaldehyde bearing an adjacent aryl group and active cyano-containing methylene compounds

被引：0

作者：

Yoshikawa, Takahiro ^{[1
,2
]}

Hayashi, Naoto ^{[2
]}

Yamada, Akihiro ^{[1
]}

Yokota, Masayuki ^{[1
]}

机构：

[1] Kongo Chem Co Ltd, Res & Dev, Himata, Toyama 9300912, Japan

[2] Univ Toyama, Grad Sch Sci & Engn, Gofuku, Toyama 9308555, Japan

来源：

TETRAHEDRON LETTERS | 2023年 / 116卷

关键词：

Knoevenagel reaction; Ortho disubstituted aldehyde; Stereochemistry; CN; p interaction; Rosuvastatin calcium; CONDENSATION-REACTIONS; STEREOCHEMISTRY; MECHANISM; KINETICS; VOLUMES;

D O I：

10.1016/j.tetlet.2022.154307

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Knoevenagel reaction between cyanoacetic acid and 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N- methanesulfonylamino)-5-pyrimidinecarboxaldehyde (1), which contains an aryl group adjacent to the formyl group in the pyrimidine-5-carbaldehyde moiety, was found to proceed stereoselectively to give an alkene product bearing cyano and phenyl groups in a cis relationship. Similar selective reactions also occurred between 1 and several active methylene compounds bearing a cyano group. An X-ray structure analysis of the alkene products and molecular orbital calculations suggested that the attractive CN/p interaction between the cyano and 4-fluorophenyl groups of 1 plays an important role in the selectivity by stabilizing the carbocation intermediates. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：4

共 11 条

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