Abstract

A novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5-a]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C–O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines of biological interest. This operation efficiently allows C–C, C–N and C–S bond formation.

A novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5-a]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C–O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines of biological interest. This operation efficiently allows C–C, C–N and C–S bond formation.

中文翻译：

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有效合成新的7-三氟甲基-2,5-二取代的吡唑并[1,5-a]嘧啶

摘要

据报道，由3-氨基吡唑和4,4,4-三氟丁-2-丙酮酸乙酯可实现三氟甲基化的3,5-二取代的吡唑并[1,5- a ]嘧啶的新型两步合成方法。合成路线开始于通过3-氨基吡唑与氟化炔烃的缩合反应一锅合成7-三氟甲基化吡唑并[1,5 - a ]嘧啶-5-酮。所获得的产物被用作直接合成的构建基块，通过C–O键活化具有优异的产率，这是一个新的具有生物学意义的氟化3,5-二取代吡唑并[1,5- a ]嘧啶的文库。该操作有效地允许C–C，C–N和C–S键的形成。

据报道，由3-氨基吡唑和4,4,4-三氟丁-2-丙酮酸乙酯可实现三氟甲基化的3,5-二取代的吡唑并[1,5- a ]嘧啶的新型两步合成方法。合成路线开始于通过3-氨基吡唑与氟化炔烃的缩合反应一锅合成7-三氟甲基化吡唑并[1,5 - a ]嘧啶-5-酮。所获得的产物被用作直接合成的构建基块，通过C–O键活化具有优异的产率，这是一个新的具有生物学意义的氟化3,5-二取代吡唑并[1,5- a ]嘧啶的文库。该操作有效地允许C–C，C–N和C–S键的形成。