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J-GLOBAL ID：201902219629405083   Reference number：19A1861746

SYNTHESIS OF DIVERSE 3-AZIDO-5-(AZIDOMETHYL)BENZENE DERIVATIVES VIA FORMAL C-H AZIDATION AND FUNCTIONAL GROUP-SELECTIVE TRANSFORMATIONS

形式的C-Hアジド化と官能基選択的変換による多様な3-アジド-5-(アジドメチル)ベンゼン誘導体の合成

Author (6)： NISHIYAMA Yoshitake (Tokyo Medical and Dental Univ. (TMDU), Tokyo, JPN) ,  MISAWA Yoshihiro (Tokyo Medical and Dental Univ. (TMDU), Tokyo, JPN) ,  HAZAMA Yuki (Tokyo Medical and Dental Univ. (TMDU), Tokyo, JPN) ,  OYA Kazuhiro (Tokyo Medical and Dental Univ. (TMDU), Tokyo, JPN) ,  YOSHIDA Suguru (Tokyo Medical and Dental Univ. (TMDU), Tokyo, JPN) ,  HOSOYA Takamitsu (Tokyo Medical and Dental Univ. (TMDU), Tokyo, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 99  Issue： 2  Page： 1053-1072  Publication year： May. 01, 2019 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *azide(organic) ,  aromatic compound ,  *nucleophilic substitution reaction ,  boration ,  elimination reaction ,  chemical reaction ,  activation ,  chemical synthesis
Semi thesaurus term： C-H bond activation ,  *Azidation

JST classification (1)： Aromatic monocyclic hydroxylamines,hydrazines and other compounds  (CF05060O)

Substance index (15)： [3-アジド-5-(アジドメチル)フェニル]メタノール ,  3-Iodo-5-azidobenzyl azide ,  3-(Bromomethyl)-5-azidobenzyl azide ,  3-Azidomethyl-5-azidobenzoic acid ,  3-(Azidomethyl)-5-azidobenzoic acid succinimidyl ester ,  3-(Azidomethyl)-5-azidobenzaldehyde ,  1-[(トシルチオ)メチル]-3-アジド-5-(アジドメチル)ベンゼン ,  N′-Hydroxy-3-(azidomethyl)-5-azidobenzamidine ,  1-アジド-3-(アジドメチル)-5-エチニルベンゼン ,  5-Diazoacetyl-3-(azidomethyl)phenyl azide ,  1-[3-azido-5-(azidomethyl)phenyl]-2-bromoethanone ,  3-(Azidomethyl)-5-azidophenol ,  3-(Azidomethyl)-5-azidoaniline ,  3-アジド-5-(アジドメチル)フェニルイソチオシアナート ,  3-(Azidomethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborole-2-yl)phenyl azide

Reference (35)：

• (a) S. Bräse, C. Gil, K. Knepper, and V. Zimmermann, Angew. Chem. Int. Ed., 2005, 44, 5188; (b) S. Bräse and K. Banert, 'Organic Azides: Syntheses and Applications', John Wiley & Sons, West Sussex, 2010; (c) Z. Yuan, G.-C. Kuang, R. J. Clark, and L. Zhu, Org. Lett., 2012, 14, 2590; (d) J. Dommerholt, O. van Rooijen, A. Borrmann, C. F. Guerra, F. M. Bickelhaupt, and F. L. van Delft, Nat. Commun., 2014, 5, 5378; (e) S. Xie, S. A. Lopez, O. Ramström, M. Yan, and K. N. Houk, J. Am. Chem. Soc., 2015, 137, 2958; (f) N. Münster, P. Nikodemiak, and U. Koert, Org. Lett., 2016, 18, 4296; (g) K. Banert, Synthesis, 2016, 48, 2361; (h) D. Huang and G. Yan, Adv. Synth. Catal., 2017, 359, 1600.
• (a) C. Wentrup, Acc. Chem. Res., 2011, 44, 393; (b) D. Intrieri, P. Zardi, A. Caselli, and E. Gallo, Chem. Commun., 2014, 50, 11440.
• (a) H. C. Kolb, M. G. Finn, and K. B. Sharpless, Angew. Chem. Int. Ed., 2001, 40, 2004; (b) J. E. Hein and V. V. Fokin, Chem. Soc. Rev., 2010, 39, 1302; (c) A. Mandoli, Molecules, 2016, 21, 1174.
• (a) C. W. Tornøse, C. Christensen, and M. Meldal, J. Org. Chem., 2002, 67, 3057; (b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, Angew. Chem. Int. Ed., 2002, 41, 2596; (c) M. Meldal and C. W. Tornøe, Chem. Rev., 2008, 108, 2952.
• (a) E. M. Sletten and C. R. Bertozzi, Angew. Chem. Int. Ed., 2009, 48, 6974; (b) M. F. Debets, C. W. J. van der Doelen, F. P. J. T. Rutjes, and F. L. van Delft, ChemBioChem, 2010, 11, 1168; (c) J. C. Jewett and C. R. Bertozzi, Chem. Soc. Rev., 2010, 39, 1272; (d) J. Dommerholt, F. P. J. T. Rutjes, and F. L. van Delft, Top. Curr. Chem., 2016, 374, 16.

Terms in the title (4)： アジド化 ,  官能基 ,  アジド ,  ベンゼン誘導体