Citation: Chen Zhi, Shi Xiao-Xiao, Ge Dong-Qin, Jiang Zhen-Zhen, Jin Qi-Qi, Jiang Hua-Jiang, Wu Jia-Shou. Facile synthesis of indoles by K2CO3 catalyzed cyclization reaction of 2-ethynylanilines in water[J]. Chinese Chemical Letters, ;2017, 28(2): 231-234. doi: 10.1016/j.cclet.2016.07.022 shu

Facile synthesis of indoles by K2CO3 catalyzed cyclization reaction of 2-ethynylanilines in water

  • Corresponding author: Wu Jia-Shou, jsw79@sina.com
  • Received Date: 12 June 2016
    Revised Date: 8 July 2016
    Accepted Date: 12 July 2016
    Available Online: 21 February 2016

Figures(3)

  • The cyclization reaction of 2-ethynyl-N-sulfonylanilides proceeded efficiently in water with the presence of a catalytic amount of K2CO3 under transition metal-free condition to give indoles in high yields. The recovery and reusability of the present catalytic system were investigated.
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    1. [1]

      (a) M. Lounasmaa, A. Tolvanen, Simple indole alkaloids and those with a nonrearranged monoterpenoid unit, Nat. Prod. Rep. 17(2000) 175-191; (b) S. Hibino, T. Choshi, Simple indole alkaloids and those with a nonrearranged monoterpenoid unit, Nat. Prod. Rep. 19(2002) 148-180; (c) M. Somei, F. Yamada, Simple indole alkaloids and those with a nonrearranged monoterpenoid unit, Nat. Prod. Rep. 21(2004) 278-311; (d) N.E. Golantsov, A.A. Festa, A.V. Karchava, M.A. Yurovskaya, Marine indole alkaloids containing an 1-(indol-3-yl) ethane-1, 2-diamine fragment, Chem. Heterocycl. Compd. 49(2013) 203-225.

    2. [2]

      (a) E. Fischer, F. Jourdan, Ueber die hydrazine der brenztraubensa üre, Ber. Deutsch. Chem. Gesell. 16(1883) 2241-2245; (b) E. Fischer, O. Hess, Synthese von indolderivaten, Ber. Deutsch. Chem. Gesell. 17(1884) 559-568.

    3. [3]

      (a) G.R. Humphrey, J.T. Kuethe, Practical methodologies for the synthesis of indoles, Chem. Rev. 106(2006) 2875-2911; (b) R. Vicente, Recent advances in indole syntheses:new routes for a classic target, Org. Biomol. Chem. 9(2011) 6469-6480; (c) S. Cacchi, G. Fabrizi, Update 1 of:synthesis and functionalization of indoles through palladium-catalyzed reactions, Chem. Rev. 111(2011) PR215-PR283; (d) Y. Oda, N. Matsuyama, K. Hirano, T. Satoh, M. Miura, Dehydrogenative synthesis of C3-azolylindoles via copper-promoted annulative direct coupling of o-alkynylanilines, Synthesis 44(2012) 1515-1520.

    4. [4]

      (a) L.B. Huang, M. Arndt, K. Gooßen, H. Heydt, L.J. Gooßen, Late transition metalcatalyzed hydroamination and hydroamidation, Chem. Rev. 115(2015) 2596-2697; (b) M. Platon, R. Amardeil, L. Djakovitch, J.C. Hierso, Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles:a focus on indole backbones, Chem. Soc. Rev. 41(2012) 3929-3968; (c) S. Cacchi, G. Fabrizia, A. Goggiamani, Copper catalysis in the construction of indole and benzo[b]furan rings, Org. Biomol. Chem. 9(2011) 641-652; (d) K. Hiroya, S. Itoh, T. Sakamoto, Mild and efficient cyclization reaction of 2-ethynylaniline derivatives to indoles in aqueous medium, Tetrahedron 61(2005) 10958-10964; (e) S.C. Song, M.N. Huang, W.J. Li, X.H. Zhu, Y.Q. Wan, Efficient synthesis of indoles from 2-alkynylaniline derivatives in water using a recyclable copper catalyst system, Tetrahedron 71(2015) 451-456; (f) K. Hiroya, S. Itoh, T. Sakamoto, Development of an efficient procedure for indole ring synthesis from 2-ethynylaniline derivatives catalyzed by Cu (II) salts and its application to natural product synthesis, J. Org. Chem. 69(2004) 1126-1136.

    5. [5]

      (a) A. Chanda, V.V. Fokin, Organic synthesis "On Water", Chem. Rev. 109(2009) 725-748; (b) R.N. Butler, A.G. Coyne, Water:nature's reaction enforcer-comparative effects for organic synthesis "In-Water" and "On-Water", Chem. Rev. 110(2010) 6302-6337; (c) M.O. Simon, C.J. Li, Green chemistry oriented organic synthesis in water, Chem. Soc. Rev. 41(2012) 1415-1427.

    6. [6]

      (a) A. Carpita, A. Ribecai, Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases, Tetrahedron Lett. 50(2009) 6877-6881; (b) A. Carpita, A. Ribecai, P. Stabile, Microwave-assisted synthesis of indole-and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts, Tetrahedron 66(2010) 7169-7178.

    7. [7]

      Z.N. Jin, H.J. Jiang, J.S. Wu. Synthesis of 2-heterocyclic substituted pyrrolidines by copper-catalyzed domino three-component decarboxylative coupling and cyclization reactions[J]. Tetrahedron Lett., 2015,56:2720-2723. doi: 10.1016/j.tetlet.2015.04.018

    8. [8]

      F. Wang, H. Liu, L.F. Cun. Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles[J]. J. Org. Chem., 2005,70:9424-9429. doi: 10.1021/jo0514826

    9. [9]

      (a) J.J. Wang, N. Soundarajan, N. Liu, K. Zimmermann, B.N. Naidu, Highly convergent synthesis of a rebeccamycin analog with benzothioeno (2, 3-a) pyrrolo (3, 4-c) carbazole as the aglycone, Tetrahedron Lett. 46(2005) 907-910; (b) A.L. Rodriguez, C. Koradin, W. Dohle, P. Knochel, Versatile indole synthesis by a 5-endo-dig cyclization mediated by potassium or cesium bases, Angew. Chem. Int. Ed. 39(2000) 2488-2490; (c) C. Koradin, W. Dohle, A.L. Rodriguez, B. Schmid, P. Knochel, Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases, Tetrahedron 59(2003) 1571-1587; (d) A.H. Stoll, P. Knochel, Preparation of fully substituted anilines for the synthesis of functionalized indoles, Org. Lett. 10(2008) 113-116; (e) Y. Kondo, S. Kojima, T. Sakamoto, General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety, J. Org. Chem. 62(1997) 6507-6511.

    10. [10]

      D.Y. Li, K.J. Shi, X.F. Mao. Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide[J]. Tetrahedron, 2014,70:7022-7031. doi: 10.1016/j.tet.2014.06.078

    11. [11]

      B. List. Proline-catalyzed asymmetric reactions[J]. Tetrahedron, 2002,58:5573-5590. doi: 10.1016/S0040-4020(02)00516-1

    12. [12]

      (a) K. Hiroya, S. Itoh, M. Ozawa, Y. Kanamori, T. Sakamoto, Efficient construction of indole rings from 2-ethynylaniline derivatives catalyzed by copper (II) salts and its application to the tandem cyclization reactions, Tetrahedron Lett. 43(2002) 1277-1280; (b) K.C. Majumdar, S. Samanta, B. Chattopadhyay, A convenient synthesis of pyrrolopyridines and 2-substituted indoles by gold-catalyzed cycloisomerization, Tetrahedron Lett. 49(2008) 7213-7216; (c) A. Yasuhara, Y. Kanamori, M. Kaneko, et al., Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride, J. Chem. Soc. Perkin Trans. 1(1999) 529-534.

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