Synthesis of 1-(pyrrolidin-2-ylmethyl)-1H-azoles and their piperidine-derived homologues

被引：1

作者：

Zhersh, Sergey ^{[1
,2
]}

Karpenko, Oleksandr V. ^{[1
]}

Ripenko, Vasyl ^{[1
]}

Tolmachev, Andrey A. ^{[1
,2
]}

Grygorenko, Oleksandr O. ^{[2
]}

机构：

[1] Enamine Ltd, UA-01103 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, Dept Chem, UA-01601 Kiev, Ukraine

来源：

CENTRAL EUROPEAN JOURNAL OF CHEMISTRY | 2014年 / 12卷 / 01期

关键词：

Azoles; Saturated nitrogen heterocycles; Molecular rigidity; Lead-oriented synthesis; Alkylation; CHIRAL IONIC LIQUIDS; MICHAEL ADDITION; ORGANOCATALYSTS; NITROOLEFINS; CHEMISTRY;

D O I：

10.2478/s11532-013-0344-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient preparation of 1-(pyrrolidin-2-yl)-1H-pyrazoles, -imidazoles, and -1H-1,2,4-triazoles, 1-(piperidin-2-yl)-1H-pyrazoles and -1H-1,2,4-triazoles, and 1-(piperidin-3-yl)-1H-1,2,4-triazoles by alkylation of azoles (viz. pyrazoles, imidazoles, and triazoles) with N-Cbz-prolinol mesylate or its analogues and subsequent deprotection is reported. The two-step method allows for synthesis of the title compounds in 16-65% yields. The utility of the procedure has been demonstrated by multigram preparation of a 15-member building block mini-library for the lead-oriented synthesis of compound libraries. These building blocks perfectly fit the definition of low-molecular-weight hydrophilic three-dimensional templates, which leave much room for the lead-oriented synthesis of the compound libraries.

引用

页码：67 / 73

页数：7

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