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.
Reaction of 4-bromo-NH-1,2,3-triazoles with alkyl halides in the presence
of K2CO3 in DMF produced the corresponding 2-substituted
4-bromo-1,2,3-triazoles in a regioselective process. Subsequent Suzuki
cross-coupling reaction provided an efficient synthesis of 2,4,5-trisubstituted
triazoles, whereas hydrogenation furnished an efficient synthesis of
2,4-disubstituted triazoles.
X.-j. Wang, K. Sidhu, L. Zhang, S. Campbell, N. Haddad, D. C. Reeves, D.
Krishnamurthy, C. H. Senanayake, Org. Lett., 2009,
11, 5460-5493.
A series of N,N′-asymmetrically substituted imidazolium iodides have been
synthesized, starting from N-arylimidazoles and the less expensive, but
less reactive, 1-chlorobutane or (3-chloropropyl)trimethoxysilane. The addition
of potassium iodide and the use of 1,2-dimethoxyethane as a solvent allowed the
synthesis of multigram quantities of these salts.
A. M. Oertel, V. Ritleng, M. J. Chetcuti, Synthesis, 2009,
1647-1650.
N-Methylimidazole is a promising catalyst for aza-Michael reactions.
Various N-heterocycles were introduced to α,β-unsaturated carbonyl compounds
employing N-methylimidazole in a highly efficient, rapid and high
yielding synthesis of N-heterocyclic derivatives.
B. K. Liu, Q. Wu, X. Q. Qian, D. S. Lv, X. F. Lin, Synthesis, 2007,
2653-2659.
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.
