Categories: C-N Bond Formation > Synthesis of substituted N-heterocycles >
N-alkylation
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In ionic liquids [Bmim][PF6] or [Bmim][BF4], a highly regioselective
N-substitution of pyrrole with alkyl halides, sulfonyl chlorides, and benzoyl
chloride gave substituted pyrroles in excellent yields. Michael addition of
pyrrole with electrophilic olefins was completed in a highly regioselective
manner to afford N-alkylpyrroles.
Z.-G. Lea, Z.-C. Chen, Y. Hu, Q.-G. Zheng Synthesis,
2004,
1951-1954.
A convenient, efficient, and selective N-Alkylation of N-acidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. In this
manner, phthalimide, indole, benzimidazole, and succinimide can be successfully
alkylated.
Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004,
208-212.
