Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation

被引：3
作者：
Lemrova, Barbora [1 ]
Malon, Michal [2 ]
Soural, Miroslav [1 ,3 ]
机构：
[1] Palacky Univ, Fac Sci, Dept Organ Chem, 17 Listopadu 12, Olomouc 77146, Czech Republic
[2] JEOL UK Ltd, JEOL House, Welwyn Garden City AL7 1LT, Herts, England
[3] Palacky Univ, Fac Med & Dent, Inst Mol & Translat Med, Hnevotinska 5, Olomouc 77900, Czech Republic
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 18期
关键词：
SOLID-PHASE SYNTHESIS; ONE-POT SYNTHESIS; TETRASUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITY; DERIVATIVES; AMINES; REARRANGEMENT; ENAMINONES; ALKALOIDS;
D O I：
10.1039/d2ob00536k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Immobilized l-aspartic acid beta-methyl ester (Fmoc-Asp(OMe)-OH) was reacted with 4-nitrobenzenesulfonyl chloride, followed by alkylation with various alpha-haloketones. The resulting intermediates were treated with potassium trimethylsilanolate, which yielded tetrasubstituted pyrroles after a one-step transformation consisting of sequential C-arylation, aldol condensation and spontaneous aromatization. The discovered synthetic strategy enables fast and simple access to pentasubstituted and functionalized pyrroles from a number of readily available starting materials.
引用
收藏
页码：3811 / 3816
页数：6
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