Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines

Katsunori Tanaka, Eric R.O. Siwu, Shinji Hirosaki, Takayuki Iwata, Risa Matsumoto, Yasutaka Kitagawa, Ambara R. Pradipta, Mitsutaka Okumura, Koichi Fukase

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Formal [4+4] reaction of the unsaturated benzyl- or allylimines, which is efficiently mediated by primary amine, provides the 2,6,9-triazabicyclo[3.3.1] nonane derivatives. Variously substituted homo- and hetero-coupling products are obtained in good to excellent yields by quite a simple procedure under mild conditions: by mixing the unsaturated aldehydes with the amines at room temperature.

Original languageEnglish
Pages (from-to)5899-5902
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number44
DOIs
Publication statusPublished - Oct 31 2012
Externally publishedYes

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Imines
Amines
Aldehydes
Derivatives
Temperature
nonane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines. / Tanaka, Katsunori; Siwu, Eric R.O.; Hirosaki, Shinji; Iwata, Takayuki; Matsumoto, Risa; Kitagawa, Yasutaka; Pradipta, Ambara R.; Okumura, Mitsutaka; Fukase, Koichi.

In: Tetrahedron Letters, Vol. 53, No. 44, 31.10.2012, p. 5899-5902.

Research output: Contribution to journalArticle

Tanaka, K, Siwu, ERO, Hirosaki, S, Iwata, T, Matsumoto, R, Kitagawa, Y, Pradipta, AR, Okumura, M & Fukase, K 2012, 'Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines', Tetrahedron Letters, vol. 53, no. 44, pp. 5899-5902. https://doi.org/10.1016/j.tetlet.2012.08.081
Tanaka, Katsunori ; Siwu, Eric R.O. ; Hirosaki, Shinji ; Iwata, Takayuki ; Matsumoto, Risa ; Kitagawa, Yasutaka ; Pradipta, Ambara R. ; Okumura, Mitsutaka ; Fukase, Koichi. / Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 44. pp. 5899-5902.
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