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Synthesis of 1H-indazole: a combination of experimental and theoretical studies

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Abstract

A new practical synthesis of 1H-indazole is presented. A previous mechanism for the cyclization step is proved to be nonfeasible and a hydrogen bond propelled mechanism is proposed. The new mechanism is suitable for similar cyclization, and a new reaction is predicted.

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References

  1. J.D. Rodgers, B.L. Johnson, H.S. Wang, R.A. Greenberg, S. EricksonViitanen, R.M. Klabe, B.C. Cordova, M.M. Rayner, G.N. Lam, C.H. Chang, Bioorg. Med. Chem. Lett. 6(24), 2919–2924 (1996)

    Article  CAS  Google Scholar 

  2. I.E. Kopka, L.S. Lin, R.A. Mumford, T. Lanza, P.A. Magriotis, D. Young, S.E. DeLaszlo, M. MacCoss, S.G. Mills, G. Van Riper, E. McCauley, K. Lyons, S. Vincent, L.A. Egger, U. Kidambi, R. Stearns, A. Colletti, Y. Teffera, S. Tong, K. Owens, D. Levorse, J.A. Schmidt, W.K. Hagmann, Bioorg. Med. Chem. Lett. 12(17), 2415–2418 (2002)

    Article  CAS  Google Scholar 

  3. R.V. Coelho, K. Schildknegt, J Labelled Compd. Rad. 50(7–8), 675–678 (2007)

    Article  CAS  Google Scholar 

  4. R. Liu, Y.M. Zhu, L.N. Qin, S.J. Ji, Synth. Commun. 38(2), 249–254 (2008)

    Article  Google Scholar 

  5. P.D. Lokhande, A. Raheem, S.T. Sabale, A.R. Chabukswar, S.C. Jagdale, Tetrahedron Lett. 48(39), 6890–6892 (2007)

    Article  CAS  Google Scholar 

  6. K. Lukin, M.C. Hsu, D. Fernando, M.R. Leanna, J. Org. Chem. 71(21), 8166–8172 (2006)

    Article  CAS  Google Scholar 

  7. C. Spiteri, S. Keeling, J.E. Moses, Org Lett 12(15), 3368–3371 (2010)

    Article  CAS  Google Scholar 

  8. T. Kylmala, A. Hamalainen, N. Kuuloja, J. Tois, R. Franzen, Tetrahedron 66(46), 8854–8861 (2010)

    Article  Google Scholar 

  9. M.J.T. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian03. Gaussian, Inc

  10. A.D. Becke, J. Chem. Phys. 98(7), 5648–5652 (1993)

    Article  CAS  Google Scholar 

  11. C.T. Lee, W.T. Yang, R.G. Parr, Phys. Rev. B 37(2), 785–789 (1988)

    Article  CAS  Google Scholar 

  12. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 157(3), 200–206 (1989)

    Article  CAS  Google Scholar 

  13. S.H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 58(8), 1200–1211 (1980)

    Article  CAS  Google Scholar 

  14. M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 255(4–6), 327–335 (1996)

    Article  CAS  Google Scholar 

  15. S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 55(1), 117–129 (1981)

    Article  CAS  Google Scholar 

  16. S. Miertus, J. Tomasi, Chem. Phys. 65(2), 239–245 (1982)

    Article  CAS  Google Scholar 

  17. K. Fukui, Acc. Chem. Res. 14(12), 363–368 (1981)

    Article  CAS  Google Scholar 

  18. H.P. Hratchian, H.B. Schlegel, J. Chem. Theory Comput. 1(1), 61–69 (2005)

    Article  CAS  Google Scholar 

  19. M. Carmeli, S. Rozen, Tetrahedron Lett. 47(5), 763–766 (2006)

    Article  CAS  Google Scholar 

  20. J.T. Strupczewski, R.C. Allen, B.A. Gardner, B.L. Schmid, U. Stache, E.J. Glamkowski, M.C. Jones, D.B. Ellis, F.P. Huger, R.W. Dunn, J. Med. Chem. 28(6), 761–769 (1985)

    Article  CAS  Google Scholar 

  21. N. Iranpoor, H. Firouzabadi, N. Nowrouzi, Tetrahedron Lett. 47(47), 8247–8250 (2006)

    Article  CAS  Google Scholar 

  22. M. Searcey, S.S. Grewal, F. Madeo, P.G. Tsoungas, Tetrahedron Lett. 44(35), 6745–6747 (2003)

    Article  CAS  Google Scholar 

  23. G. Stokker, J. Org. Chem. 48(15), 2613–2615 (1983)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Chemical Engineering, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, China

    Xinzhi Chen, Shaodong Zhou, Chao Qian & Chaohong He

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  1. Xinzhi Chen
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  2. Shaodong Zhou
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  3. Chao Qian
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  4. Chaohong He
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Correspondence to Chao Qian.

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Chen, X., Zhou, S., Qian, C. et al. Synthesis of 1H-indazole: a combination of experimental and theoretical studies. Res Chem Intermed 38, 1619–1628 (2012). https://doi.org/10.1007/s11164-012-0488-y

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  • DOI: https://doi.org/10.1007/s11164-012-0488-y

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