First synthesis of tert-butyl-substituted [1,2,4]triazino[5,6-b]indole-3-thiols and indolo[2,3-b]quinoxalines

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• 作者：Mingyue Lv ; Hongmei Zheng ; Yang Li ; Wentao Gao
• 关键词：tert ; Butyl group ; [1 ; 2 ; 4]Triazino[5 ; 6 ; b]indole ; Indolo[2 ; 3 ; b]quinoxaline ; Isatin ; Benzene ; 1 ; 2 ; diamine ; Thiosemicarbazide
• 刊名：Research on Chemical Intermediates
• 出版年：2015
• 出版时间：October 2015
• 年：2015
• 卷：41
• 期：10
• 页码：6927-6939
• 全文大小：1,035 KB
• 参考文献：1.J.L. Kgokong, P.P. Smith, G.M. Matsabisa, Bioorg. Med. Chem. 13, 2935 (2005)CrossRef
  2.S.M. Shelke, S.H. Bhosale, Bioorg. Med. Chem. Lett. 20, 4661 (2010)CrossRef
  3.L. Gupta, N. Sunduru, A. Verma, S. Srivastava, S. Gupta, N. Goyal, P.M.S. Chauhan, Eur. J. Med. Chem. 45, 2359 (2010)CrossRef
  4.P.B. Arimondo, B. Baldeyrou, W. Laine, C. Bal, F.A. Alphonse, S. Routier, G. Coudert, J.Y. M茅rour, P. Colson, C. Houssier, C. Bailly, Chem. Biol. Interact. 138, 59 (2001)CrossRef
  5.R. Sharma, A.K. Pandey, R. Shivahare, K. Srivastava, S. Gupta, P.M.S. Chauhan, Bioorg. Med. Chem. Lett. 24, 298 (2014)CrossRef
  6.K. Ramesh, S.N. Murthy, K. Karnakar, Y.V.D. Nageswar, Tetrahedron Lett. 52, 4734 (2011)CrossRef
  7.E.S.H.E. Ashry, E.S. Ramadan, H.M.A. Hamid, M. Hagar, Synlett 723 (2004)
  8.K. Manna, Y.K. Agrawal, Bioorg. Med. Chem. Lett. 19, 2688 (2009)CrossRef
  9.A.V. Ivachtchenko, A.P. Il鈥檡in, V.V. Kobak, D.A. Zolotarev, L.V. Boksha, A.S. Trifilenkov, D.M. Ugoleva, J. Comb. Chem. 4, 419 (2002)CrossRef
  10.K.R.J. Thomas, P. Tyagi, J. Org. Chem. 75, 8100 (2010)CrossRef
  11.P. Tyagi, A. Venkateswararao, K.R.J. Thomas, J. Org. Chem. 76, 4571 (2011)CrossRef
  12.A. Moreau, P.N.P. Rao, E.E. Knaus, Bioorg. Med. Chem. 14, 5340 (2006)CrossRef
  13.N.T. Huy, K. Mizunuma, K. Kaur, N.T.T. Nhien, M. Jain, D.T. Uyen, S. Harada, R. Jain, K. Kamei, Antimicrob. Agents Chemother. 51, 2842 (2007)CrossRef
  14.M. Murakata, M. Kimura, Tetrahedron Lett. 51, 4950 (2010)CrossRef
  15.J. Vinsova, K. Cermakova, A. Tomeckova, M. Ceckova, J. Jampilek, P. Cermak, J. Kunes, M. Dolezal, F. Staud, Bioorg. Med. Chem. 14, 5850 (2006)CrossRef
  16.M. Inagaki, S. Matsumoto, T. Tsuri, J. Org. Chem. 68, 1128 (2003)CrossRef
  17.T. Duan, K. Fan, C. Zhong, T. Peng, J. Qin, X. Chen, RSC Adv. 2, 7081 (2012)CrossRef
  18.艁. 艁apok, A. Siudak, M. Nowakowska, Tetrahedron Lett. 54, 3816 (2013)CrossRef
  19.Y. Li, W.T. Gao, Syn. Commun. 42, 2067 (2012)CrossRef
  20.Y. Li, X.Y. Tao, G.H. Lin, W.T. Gao, Heterocycl. Commun. 18, 207 (2012)
  21.R.E. Dolle, K.H. Nelson Jr, J. Comb. Chem. 1, 235 (1999)CrossRef
  22.H. Zhang, Y. Li, W.T. Gao, Helv. Chim. Acta 96, 2134 (2013)CrossRef
  23.W.T. Gao, X.D. Xing, Y. Li, S. Lan, Tetrahedron 70, 2180 (2014)CrossRef
  24.T. Sandmeyer, Helv. Chim. Acta 2, 234 (1919)CrossRef
  25.D.D. Kenning, K.A. Mitchell, T.R. Calhoun, M.R. Funfar, D.J. Sattler, S.C. Rasmussen, J. Org. Chem. 67, 9073 (2002)CrossRef
  
• 作者单位：Mingyue Lv (1)
  Hongmei Zheng (1)
  Yang Li (1)
  Wentao Gao (1)
  
  1. Institute of Superfine Chemicals, Bohai University, Jinzhou, 121000, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

In this investigation, the first introduction of a tert-butyl group into [1,2,4]triazino[5,6-b]indole and indolo[2,3-b]quinoxaline systems, leading to a series of structurally novel 8-(t-butyl)-5H-[1,2,4]triazino[5,6-b]indole-3-thiol and 9-(t-butyl)-6H-indolo[2,3-b]quinoxaline derivatives, has been achieved by condensation of tert-butyl-substituted isatins with benzene-1,2-diamine or thiosemicarbazide. The molecular structures of these newly synthesized compounds were elucidated on the basis of elemental analysis and spectral data. Keywords tert-Butyl group [1,2,4]Triazino[5,6-b]indole Indolo[2,3-b]quinoxaline Isatin Benzene-1,2-diamine Thiosemicarbazide