Chemo- and Regioselective Synthesis of 3,4-Dihydropyrimidin-4-ones from 4,5-Dihydro-1,2,4-oxadiazoles and Chromium Alkoxy Alkynyl Fischer Carbene Complexes

由4,5-二氢-1,2,4-噁二唑和铬烷氧基炔基费歇尔卡宾配合物化学选择性和区域选择性合成3,4-二氢嘧啶-4-酮

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Abstract

A completely chemo- and regioselective synthesis of pyrimidin-4(3H)-ones by the reaction between 4,5-dihydro-1,2,4-oxadiazoles and chromium alkoxy alkynyl Fischer carbene complexes is reported. Overall, it is a formal (3+3) cycloaddition in which 4,5-dihydro-1,2,4-oxadiazoles participate for the first time in the intermolecular formation of six-membered heterocycles. Three points of diversity have been explored, and usually, synthetically useful isolated yields are reached, including one example at the gram scale. A reasonable mechanism, supported by DFT calculations, is proposed.

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