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J-GLOBAL ID：200902221089927615   Reference number：06A0910617

MICROWAVE-ASSISTED CYCLOADDITION REACTION OF AZIDES TO N-SUBSTITUTED 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONES

アジドのN-置換-2-アザビシクロ[2.2.1]ヘプタ-5-エン-3-オン類へのマイクロ波支援環状付加反応

Author (4)： ISHIKURA Minoru (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  HASUNUMA Miyako (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  YAMADA Koji (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  YANADA Reiko (Hiroshima International Univ., Hiroshima, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 68  Issue： 11  Page： 2253-2257  Publication year： Nov. 01, 2006 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： azide(organic) ,...
Semi thesaurus term： bridged compound

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JST classification (1)： Condensed derivatives of pyrroles  (CF07077C)

Substance index (14)： (1α,4α)-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]hepta-5-ene-3-one ,  (1α,4α)-2-(tert-Butyldimethylsilyl)-2-azabicyclo[2.2.1]hepta-5-ene-3-one ,  (1α,2β,4β,5α)-3-Tosyl-7-oxo-3,6-diazatricyclo[3.2.1.0^2,4]octane-6-carboxylic acid tert-butyl ester ,  (1α,2β,4β,5α)-3-Tosyl-6-(tert-butyldimethylsilyl)-3,6-diazatricyclo[3.2.1.0^2,4]octane-7-one ,  (1α,2β,4β,5α)-3-(Diphenoxyphosphinyl)-7-oxo-3,6-diazatricyclo[3.2.1.0^2,4]octane-6-carboxylic acid tert-butyl ester ,  (1α,2β,4β,5α)-3-(Diphenoxyphosphinyl)-6-(tert-butyldimethylsilyl)-3,6-diazatricyclo[3.2.1.0^2,4]octane-7-one ,  (1α,2β,6β,7α)-5-Phenyl-9-oxo-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-3-ene-8-carboxylic acid tert-butyl ester ,  (1α,2β,6β,7α)-5-Phenyl-8-(tert-butyldimethylsilyl)-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-3-ene-9-one ,  (1α,2β,6β,7α)-5-Benzyl-9-oxo-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-3-ene-8-carboxylic acid tert-butyl ester ,  (1α,2β,6β,7α)-5-Benzyl-8-(tert-butyldimethylsilyl)-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-3-ene-9-one ,  (1α,2β,6β,7α)-3-Phenyl-9-oxo-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-4-ene-8-carboxylic acid tert-butyl ester ,  (1α,2β,6β,7α)-3-Phenyl-8-(tert-butyldimethylsilyl)-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-4-ene-9-one ,  (1α,2β,6β,7α)-3-Benzyl-9-oxo-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-4-ene-8-carboxylic acid tert-butyl ester ,  (1α,2β,6β,7α)-3-Benzyl-8-(tert-butyldimethylsilyl)-3,4,5,8-tetraazatricyclo[5.2.1.0^2,6]deca-4-ene-9-one

Reference (10)：

• M. K. Gurjar, S. Bera, R. R. Joshi, and R. A. Joshi, Heterocycles, 2003, 60, 2293; M. Ishikura, M. Hasunuma, and M. Saijo, Heterocycles, 2004, 63, 5; M. Ishikura, M. Hasunuma, and K. Yanada, Heterocycles, 2005, 65, 2587; R. J. Brea, M. Amorin, L. Castedo, and J. R. Granja, Angew. Chem. Int. Ed., 2005, 44, 5710.
• a) N. Katagiri, Y. Yamatoya, and M. Ishikura, Tetrahedron Lett., 1999, 40, 9069; b) M. Ishikura, A. Murakami, and N. Katagiri, Org. Biomol. Chem., 2003, 1, 452; c) M. Ishikura, K. Matsumoto, M. Hasunuma, and N. Katagiri, Heterocycles, 2003, 60, 2737; d) M. Ishikura, K. Matsumoto, and A. Murakami, Heterocycles, 2004, 64, 241.
• M. Ishikura, S. Kudo, A. Hino, N. Ohnuki, and N. Katagiri, Heterocycles, 2000, 53, 1499.
• R. Huisgen, L. MObius, G. Muller, H. Stangl, G. Szeimies, and J. M. Vernon, Chem. Ber., 1965, 98, 3992.
• There is one example of cycloaddition reaction of phenyl azide to 1 (R= H) at 90°C in CH₂Cl₂; J. R. Malpass, D. Belkacemi, G. A. Griffith, and M. D. Robertson, ARKIVOC, 2002,(vi), 164.

Terms in the title (5)： アジド ,  置換 ,  マイクロ波 ,  支援 ,  環状付加反応