Abstract

4-(2,2-Difluoroethylamino)-3-(heteroarylmethyl)-5,5-disubstituted furan-2(5H)-ones were regioselectively synthesized via C-3 alkylation of 4-(2,2-difluoroethylamino)-5,5-disubstituted furan-2(5H)-ones with heteroarylmethyl chlorides using Cs₂CO₃ as a base in 62–85% yields. Their structures were characterized by ¹H and ¹³C NMR, HRMS (ESI), and X-ray diffraction. This C-alkylation selectivity was rationalized by bulky hindrance and electron-withdrawing effects.

4-(2,2-Difluoroethylamino)-3-(heteroarylmethyl)-5,5-disubstituted furan-2(5H)-ones were regioselectively synthesized via C-3 alkylation of 4-(2,2-difluoroethylamino)-5,5-disubstituted furan-2(5H)-ones with heteroarylmethyl chlorides using Cs₂CO₃ as a base in 62–85% yields. Their structures were characterized by ¹H and ¹³C NMR, HRMS (ESI), and X-ray diffraction. This C-alkylation selectivity was rationalized by bulky hindrance and electron-withdrawing effects.

中文翻译：

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Cs2CO3促进4-[（2,2-二氟乙基）氨基] -5,5-二取代的呋喃2（5H）-与杂芳基甲基氯的C-3烷基化

摘要

通过4-（2,2-二氟乙基氨基）-5的C-3烷基化区域选择性地合成4-（2,2-二氟乙基氨基）-3-（杂芳基甲基）-5,5-二取代的呋喃-2（5H）-，以Cs ₂ CO ₃为碱的带有杂芳基甲基氯的5-二取代呋喃2（5 H）-酮，产率为62-85％。它们的结构通过¹ H和¹³ C NMR，HRMS（ESI）和X射线衍射表征。该C-烷基化选择性通过大的位阻和吸电子效应而合理化。

通过4-（2,2-二氟乙基氨基）-5的C-3烷基化区域选择性地合成4-（2,2-二氟乙基氨基）-3-（杂芳基甲基）-5,5-二取代的呋喃-2（5H）-，以Cs ₂ CO ₃为碱的带有杂芳基甲基氯的5-二取代呋喃2（5 H）-酮，产率为62-85％。它们的结构通过¹ H和¹³ C NMR，HRMS（ESI）和X射线衍射表征。该C-烷基化选择性通过大的位阻和吸电子效应而合理化。