从单一前体制备多种三氟甲基杂环。

Diverse trifluoromethyl heterocycles from a single precursor.

机构信息

School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

出版信息

J Org Chem. 2012 Feb 3;77(3):1396-405. doi: 10.1021/jo202201w. Epub 2012 Jan 20.

DOI:10.1021/jo202201w

Abstract

Ethyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate is a highly versatile intermediate for the synthesis of a wide range of trifluoromethyl heterocycles. With the use of rhodium(II) or copper(II) catalyzed carbene X-H insertion reactions as key steps, a diverse set of trifluoromethyl-oxazoles, -thiazoles, -imidazoles, -1,2,4-triazines, and -pyridines are available from the diazoketoester, either directly in a single step or with just one additional step.

摘要

2-重氮-4,4,4-三氟-3-氧代丁酸乙酯是合成广泛的三氟甲基杂环的多功能中间体。通过使用铑（II）或铜（II）催化的卡宾 X-H 插入反应作为关键步骤，可以从重氮酮酯直接一步或仅通过一步额外步骤获得各种三氟甲基-恶唑、-噻唑、-咪唑、-1,2,4-三嗪和-吡啶。