Pyrrole and Oligopyrrole Synthesis by 1,3-Dipolar Cycloaddition of Azomethine Ylides with Sulfonyl Dipolarophiles
Pyrrole and Oligopyrrole Synthesis by 1,3-Dipolar Cycloaddition of Azomethine Ylides with Sulfonyl Dipolarophiles
复制标题
DOI：
10.1002/chem.201000742
复制
发表时间：
2010-01-01
影响因子：
4.3
通讯作者：
Carlos Carretero, Juan
中科院分区：
文献类型：
--
作者：
Robles-Machin, Rocio;Lopez-Perez, Ana;Carlos Carretero, Juan
一种用于合成官能化的。通过偶氮甲亚胺叶立德的1.3-偶极环加成反应合成了取代的吡咯。该反应是基于金属催化的α-亚氨基酯与磺酰基亲偶极试剂的环加成反应，然后通过碱促进的磺酰基消除反应。β-亚磺基酮。和β-磺酰基丙烯酸酯这种方法可以在迭代和直接的结构中应用于低聚吡咯。从联吡咯到p-五吡咯已经设计了迭代的[n+1]和[n+2]方法，后者涉及从基于吡咯基的双（亚氨基酯）
A procedure for the synthesis of functionalized. substituted pyrroles by 1.3-dipolar cycloaddition of azomethine ylides has been developed This protocol is based on the metal-catalyzed cycloaddition of alpha-iminoesters with sulfonyl dipolarophiles, followed by the base-promoted elimination of the sulfonyl groups A wide variety of 2.5-disubstituted and 2.3,5- and 2,4.5-trisubstituted pyrroles have been prepared in satisfactory yields from 1,2-bis(sulfonyl ethylene). beta-sulfonylenones. and beta-sulfonylacrylates This method can be applied in an iterative and straightforward in to the construction of oligopyrroles. from bipyrroles to p pentapyrroles Iterative [n+1] and [n+2] approaches have been devised, the latter involves double 1,3-dipolar cycloaddition from pyrrolyl-based bis(iminoesters)