Art

J-GLOBAL ID：201802287680169171   Reference number：18A1846260

SILICA GEL-ASSISTED PREPARATION OF (BROMO)(CHLORO)(IODO)BENZO[b]THIOPHENES BEARING HALOGEN ATOMS AT THE 2-, 4-, AND 7-POSITIONS

2-,4-,および7-位にハロゲン原子を有する(ブロモ)(クロロ)(ヨード)ベンゾ[b]チオフェン類のシリカゲル介在調製

Author (5)： MIKAMI Shinichi (Tohoku Univ., Miyagi, JPN) ,  TANAKA Hiroki (Tohoku Univ., Miyagi, JPN) ,  KISHI Hiroki (Tohoku Univ., Miyagi, JPN) ,  YOSHIDA Shuhei (Tohoku Univ., Miyagi, JPN) ,  TOYOTA Kozo (Tohoku Univ., Miyagi, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 96  Issue： 9  Page： 1529-1548  Publication year： Sep. 01, 2018 
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： polynuclear aromatic compound ,  sulfur heterocyclic compound ,  chemical synthesis ,  *Silica Gel ,  sulfide (organic) ,  acetylenic compound ,  cycloalkane ,  bridged compound ,  aromatic chlorine compound ,  aromatic bromine compound ,  aromatic iodine compound ,  adamantane derivative ,  *Benzothiophene derivatives

JST classification (1)： Condensed derivatives of thiophenes  (CF07075U)

Substance index (13)： 2,4-ジブロモ-7-クロロベンゾ[b]チオフェン ,  2-クロロ-4-ブロモ-7-ヨードベンゾ[b]チオフェン ,  2-Chloro-4-iodo-7-bromobenzo[b]thiophene ,  2-ブロモ-4-クロロ-7-ヨード-1-ベンゾチオフェン ,  2-ヨード-4-クロロ-7-ブロモベンゾ[b]チオフェン ,  4,7-Dibromo-1-benzothiophene ,  4-クロロ-7-ブロモベンゾ[b]チオフェン ,  4-クロロ-7-ヨードベンゾ[b]チオフェン ,  4-Bromo-7-chloro-2-iodobenzo[b]thiophene ,  4-ブロモ-7-クロロベンゾ[b]チオフェン ,  4-Bromo-7-iodo-1-benzothiophene ,  4-ヨード-7-クロロベンゾ[b]チオフェン ,  4-ヨード-7-ブロモベンゾ[b]チオフェン

Reference (15)：

• (a) B. Godoi, R. F. Schumacher, and G. Zeni, Chem. Rev., 2011, 111, 2937; (b) J. Nakayama, ‘Thiophenes and their Benzo Derivatives: Synthesis’ in ‘Comprehensive Heterocyclic Chemistry II,’ Vol. 2, ed. by C. W. Bird, Elsevier, Oxford, 1996, pp. 607-677; (c) C. M. Rayner and M. A. Graham, ‘Product Class 4: Benzo[b]thiophenes’ in ‘Science of Synthesis,’ Vol. 10, ed. by E. J. Thomas, Georg Thieme, Stuttgart, 2000, p 155.
• (a) For a recent review, see: R. S. Keri, K. Chand, S. Budagumpi, S. B. Somappa, S. A. Patil, and B. M. Nagaraja, Eur. J. Med. Chem., 2017, 138, 1002; (b) Raloxifene-related compounds, for example: A. D. Palkowitz, A. L. Glasebrook, K. J. Thrasher, K. L. Hauser, L. L. Short, D. L. Phillips, B. S. Muehl, M. Sato, P. K. Shetler, G. J. Cullinan, T. R. Pell, and H. U. Bryant, J. Med. Chem., 1997, 40, 1407.
• (a) K. Takimiya, I. Osaka, T. Mori, and M. Nakano, Acc. Chem. Res., 2014, 47, 1493; (b) L. Ye, S. Zhang, L. Huo, M. Zhang, and J. Hou, Acc. Chem. Res., 2014, 47, 1595; (c) M. J. Kang, I. Doi, H. Mori, E. Miyazaki, K. Takimiya, M. Ikeda, and H. Kuwabara, Adv. Mater., 2011, 23, 1222; (d) C.-C. Ko, W. H. Lam, and V. W.-W. Yam, Chem. Commun., 2008, 5203; (e) N. S. Baek, S. K. Hau, H.-L. Yip, O. Acton, K.-S. Chen, and A. K.-Y. Jen, Chem. Mater., 2008, 20, 5734; (f) T. Okamoto, K. Kudoh, A. Wakamiya, and S. Yamaguchi, Chem. Eur. J., 2007, 13, 548; (g) Y. Li, Y. Wu, P. Liu, M. Birau, H. Pan, and B. S. Ong, Adv. Mater., 2006, 18, 3029.
• (a) M. Sainsbury, Heterocyclic Chemistry, Wiley, New York, 2002; (b) R. Beugelmans, M. Bois-Choussy, and B. Boudet, Tetrahedron, 1983, 39, 4153; (c) S.-M. Yang, J.-J. Shie, J.-M. Fang, S. K. Nandy, H.-Y. Chang, S.-H. Lu, and G. Wang, J. Org. Chem., 2002, 67, 5208; (d) R. E. Mewshaw, S. M. Bowen, H. A. Harris, Z. B. Xu, E. S. Manas, and S. T. Cohn, Bioorg. Med. Chem. Lett., 2007, 17, 902; (e) T. Kashiki, S. Shinamura, M. Kohara, E. Miyaaki, K. Takimiya, M. Ikeda, and H. Kuwabara, Org. Lett., 2009, 11, 2473; (f) K. Yoshida, H. Shida, H. Takahashi, and A. Yanagisawa, Chem. Eur. J., 2011, 17, 344; (g) K. Yan, D. Yang, M. Zhang, W. Wei, Y. Liu, L. Tian, and H. Wang, Synlett, 2015, 1890.
• (a) R. C. Larock and D. Yue, Tetrahedron Lett., 2001, 42, 6011; (b) B. L. Flynn, P. Verdier-Pinard, and E. Hamel, Org. Lett., 2001, 3, 651; (c) M. Jacubert, A. Tikad, O. Provot, A. Hamze, J.-D. Brion, and M. Alami, Eur. J. Org. Chem., 2010, 4492; (d) M. Nakano, K. Niimi, E. Miyazaki, I. Osaka, and K. Takimiya, J. Org. Chem., 2012, 77, 8099; (e) Y. Chen, C. Liu, H. Tian, C. Bao, X. Zhang, D. Yan, Y. Geng, and F. Wang, Macromol. Rapid Commun., 2012, 33, 1759; (f) K. Goswami, S. Paul, S. T. Bugde, and S. Sinha, Tetrahedron, 2012, 68, 280; (g) Y. Kong, L. Yu, L. Fu, J. Cao, G. Lai, Y. Cui, Z. Hu, and G. Wang, Synthesis, 2013, 45, 1975.

Terms in the title (4)： ハロゲン原子 ,  チオフェン類 ,  シリカゲル ,  調製