jo9b00596_si_001.pdf (6.98 MB)

Synthesis of Multisubstituted Pyrroles from Enolizable Aldehydes and Primary Amines Promoted by Iodine

Download (6.98 MB)
journal contribution
posted on 16.04.2019 by Wenbo Huang, Shaomin Chen, Zhiyan Chen, Meie Yue, Minghao Li, Yanlong Gu
1,2,4-Trisubstituted pyrroles were synthesized from enolizable aliphatic aldehydes and primary aliphatic amines by using iodine as the dual Lewis acid/mild oxidant. In the presence of 3.0 equiv of TBHP, enolizable α,β-unsaturated aldehyde, for example, cocal reacted with aromatic primary amines to form C2-iodized N-arylpyrroles. An acetal-containing pyrrole was successfully prepared from 4-aminobutyraldehyde diethyl acetal, which can be converted easily to 5,6,7,8-tetrahydroindolizine derivatives.