Abstract

1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2H-azirine ring expansion strategy. The primary products, 3-aryl-2-(methoxycarbonyl)-4-(pyridin-1-ium-1-yl)-5-(trifluoromethyl)pyrrol-1-ides, can be hydrogenated by H₂/PtO₂ to form alkyl 3-aryl-4-(piperidin-1-yl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates and transformed into alkyl 4-amino-3-aryl-1-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates via methylation/hydrazinolysis.

1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2H-azirine ring expansion strategy. The primary products, 3-aryl-2-(methoxycarbonyl)-4-(pyridin-1-ium-1-yl)-5-(trifluoromethyl)pyrrol-1-ides, can be hydrogenated by H₂/PtO₂ to form alkyl 3-aryl-4-(piperidin-1-yl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates and transformed into alkyl 4-amino-3-aryl-1-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates via methylation/hydrazinolysis.

中文翻译：

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合成4-氨基-5-（三氟甲基）-1H-吡咯-2-羧酸烷基酯的Azirine策略

摘要

1-（3,3,3-三氟-2,2-二羟丙基）吡啶鎓-1-溴化物用作含三氟甲基的结构单元，用于基于2 H-叠氮基扩环策略制备三氟甲基取代的氨基吡咯。主要产物3-芳基-2-（甲氧基羰基）-4-（吡啶-1-基-1-基）-5-（三氟甲基）吡咯-1-化物可通过H ₂ / PtO ₂氢化形成3-芳基-4-（哌啶-1-基）-5-（三氟甲基）-1 H-吡咯-2-羧酸烷基酯并转化成4-氨基-3-芳基-1-甲基-5-（三氟甲基）烷基-1 H-吡咯-2-羧酸盐通过甲基化/肼解作用。

1-（3,3,3-三氟-2,2-二羟丙基）吡啶鎓-1-溴化物用作含三氟甲基的结构单元，用于基于2 H-叠氮基扩环策略制备三氟甲基取代的氨基吡咯。主要产物3-芳基-2-（甲氧基羰基）-4-（吡啶-1-基-1-基）-5-（三氟甲基）吡咯-1-化物可通过H ₂ / PtO ₂氢化形成3-芳基-4-（哌啶-1-基）-5-（三氟甲基）-1 H-吡咯-2-羧酸烷基酯并转化成4-氨基-3-芳基-1-甲基-5-（三氟甲基）烷基-1 H-吡咯-2-羧酸盐通过甲基化/肼解作用。