Synthesis of 1,3-and 1,2,3-functionalized pyrroles via Ir(I)-catalyzed vinylation of allyl alcohols

被引:6
作者
Alavez-Rosas, David [1 ]
Maldonado-Dominguez, Mauricio [1 ]
Gonzalez-Antonio, Oscar [1 ]
Romero-Avila, Margarita [1 ]
Mendez-Stivalet, Jos [1 ]
Flores-Perez, Blas [1 ]
机构
[1] Univ Nacl Autonoma Mexico, Sch Chem, Ciudad Univ, Mexico City 04510, DF, Mexico
关键词
allyl alcohols; pyrroles; Claisen rearrangement; ozonolysis; ONE-POT SYNTHESIS; SUBSTITUTED PYRROLES; 1,4-DICARBONYL COMPOUNDS; CLAISEN REARRANGEMENT; CARBONYL-COMPOUNDS; SULFURIC-ACID; IN-VIVO; DERIVATIVES; EFFICIENT; CATALYST;
D O I
10.1007/s10593-017-2087-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the preparation of 1,3-disubstituted and 1,2,3-trisubstituted pyrroles was developed through a sequence involving O-vinylation of allyl alcohols followed by Claisen rearrangement and further ozonolysis, concurring in a Paal-Knorr reaction with primary amines. Hg(II) and Ir(I) catalysts and different vinylating reagents were tested. The best results were consistently obtained with the [Ir(cod)Cl](2)-vinyl acetate system. The featured methodology gives access to functionalized pyrroles in overall good yields, whose chemical architecture may awake interest for assorted applications.
引用
收藏
页码:526 / 531
页数:6
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