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Paper | Regular issue | Vol 55, No. 12, 2001, pp.2305-2313
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9339
Novel Formaldehyde-mediated Dimerization Reaction of N-Alkyl-1-naphthylamine Derivatives under Mild/Neutral Conditions; Application to Synthesis of Naphthylamine-derived Macrocycles

Hiroyasu Takahashi, Yuichi Hashimoto, and Kazuo Nagasawa*

*Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan


The dimerization reaction of N-methyl-1-naphthylamine (1) with formaldehyde is described. Reaction of 1 with formaldehyde under mild/neutral conditions gave bis-4-(1-N-methylaminonaphthyl)methane (2) in high yield as a single dimerization product. This formaldehyde-mediated aromatic condensation reaction is chemo- and regio-selective, and it takes place particularly with N-monoalkyl-1-naphthylamines as substrates. The novel naphthylamine-derived macrocyclic compounds 1,6,28,33-tetraaza-[]paranaphthalenophane (13a) and 1,13-diaza[13,1]paranaphthaleno-phane (12c) were synthesized by application of this formaldehyde-mediated mild/neutral condensation reaction as the key step.