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Synthesis 1995; 1995(5): 498-500
DOI: 10.1055/s-1995-3949
short paper
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1,3-Dipolar Cycloaddition of Nitrile Functions with Nitrones under High Pressure Conditions. A New and Direct Synthesis of 2,3-Dihydro-1,2,4-Oxadiazole Derivatives

Yang Yu, Hiromi Fujita, Masatomi Ohno, Shoji Eguchi*
  • *Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-01, Japan, Fax +81(052)7893199
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Publication Date:
31 December 2000 (online)

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Usual nitrile functions underwent 1,3-dipolar cycloaddition reactions with 4-azahomoadamant-4-ene N-oxides 1 and 2, 5,5-dimethylpyrroline N-oxide (3), and benzylidenephenylamine N-oxide (4) smoothly under high pressure conditions to provide a new and direct method for synthesis of 2,3-dihydro-1,2,4-oxadiazole (Δ 4-1,2,4-oxadiazoline) derivatives.

1,3-dipolar cycloaddition - nitrone - nitrile - high pressure - oxadiazoline