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Efficient and Mild Protocol for the Synthesis of 4(3)‐Substituted 3(4)‐Nitro‐1 H ‐pyrroles and 3‐Substituted 4‐Methyl‐2‐tosyl‐1 H ‐pyrroles from Nitroolefins and Tosylmethyl Isocyanide in Ionic Liquids
Author(s) -
Qin Jie,
Zhang Ji,
Wu Bo,
Zheng Zhangguo,
Yang Meng,
Yu Xiaoqi
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990300
Subject(s) - chemistry , ionic liquid , anhydrous , nitro , tosyl , bromide , base (topology) , solvent , organic chemistry , medicinal chemistry , catalysis , alkyl , mathematical analysis , mathematics
A mild and convenient method for the synthesis of 4(3)‐substituted 3(4)‐nitro‐1 H ‐pyrroles and 3‐substituted 4‐methyl‐2‐tosyl‐1 H ‐pyrroles from nitroolefins and tosylmethyl isocyanide (TosMIC) in ionic liquid 1‐butyl‐3‐methylimidazolium bromide ([bmIm]Br) was developed. The reactions were performed at room temperature with KOH as base with good yields in a short time (about 2 h). Some tough conditions, such as absolutely anhydrous organic solvents, low temperature, hazardous and expensive strong base or organic base, were not needed. The yields of 4(3)‐substituted 3(4)‐nitro‐1 H ‐pyrroles were moderate, but excellent yields were achieved for the preparation of 3‐substituted 4‐methyl‐2‐tosyl‐1 H ‐pyrroles. This strategy was quite general and it worked in a broad range of nitroolefins with aromatic, aliphatic or heterocyclic substituents. The recovered ionic liquid could be reused as solvent for several times without significant decrease of reaction yields.