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Synlett 1995; 1995(9): 947-948
DOI: 10.1055/s-1995-5139
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A Simple Synthetic Method of [3.3] Azacyclophanes by Alkylation of Cyanamide

Gang Wen, Michiko Matsunaga, Tomonori Matsunaga, Hiroyuki Takemura, Teruo Shinmyozu*
  • *Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-81, Japan
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Publication Date:
31 December 2000 (online)

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Dialkylation reaction of commercially available cyanamid with the corresponding bromomethyl compounds proceeds smoothly in the presence of a phase-transfer catalyst in a mixture of toluene-water or dichloromethane-water under mild alkaline conditions, and affords N,N’-dicyano[3.3]azacyclophanes and their higher homologs in good to moderate yields. The two-step reaction involving the coupling followed by decyanation of the N-cyano groups provides a new, simple, synthetic method of azacyclophanes, especially for the sterically constrained or acid sensitive azacyclophanes.

Cynamide - Azacyclophanes - Cyclophanes - N-Alkylation - Coupling Reactions