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J Org Chem. 2013 Jul 5;78(13):6775-81. doi: 10.1021/jo400834h. Epub 2013 Jun 24.

Sodium hydroxide catalyzed N-alkylation of (hetero) aromatic primary amines and N1,C5-dialkylation of 4-phenyl-2-aminothiazoles with benzyl alcohols.

Author information

1
Academy of Scientific & Innovative Research, CSIR-Central Salt & Marine Chemicals Research Institute, G.B. Marg, Bhavnagar-364 002, Gujarat, India.

Abstract

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.

PMID:
23768027
DOI:
10.1021/jo400834h
[Indexed for MEDLINE]

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