English

• 1. [1] (a) D. Kumar, M. Kumar, K.H. Chang, et al., An expeditious synthesis and anticancer activity of novel 4-(3'-indolyl)oxazoles, Eur. J. Med. Chem. 45 (2010) 1244- 1249;[1] (a) D. Kumar, M. Kumar, K.H. Chang, et al., An expeditious synthesis and anticancer activity of novel 4-(3'-indolyl)oxazoles, Eur. J. Med. Chem. 45 (2010) 1244- 1249;

  2. [2]

     (b) Z. Jin, Muscarine, imidazole, oxazole, and thiazole alkaloids, Nat. Prod. Rep. 28 (2011) 1143-1191;(b) Z. Jin, Muscarine, imidazole, oxazole, and thiazole alkaloids, Nat. Prod. Rep. 28 (2011) 1143-1191;

  3. [3]

     (c) V.S.C. Yeh, Recent advances in the total syntheses of oxazole-containing natural products, Tetrahedron 60 (2004) 11995-12042;(c) V.S.C. Yeh, Recent advances in the total syntheses of oxazole-containing natural products, Tetrahedron 60 (2004) 11995-12042;

  4. [4]

     (d) B. Wang, T. Hansen, T. Wang, et al., Total synthesis of phorboxazole A via de novo oxazole formation: strategy and component assembly, J. Am. Chem. Soc. 133 (2011) 1484-1505.(d) B. Wang, T. Hansen, T. Wang, et al., Total synthesis of phorboxazole A via de novo oxazole formation: strategy and component assembly, J. Am. Chem. Soc. 133 (2011) 1484-1505.

  5. [2] (a) R. Misra, H.Y. Xiao, K. Kim, et al., N-(cycloalkylamino)acyl-2-aminothiazole inhibitors of cyclin-dependent kinase 2. N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl] methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide (BMS-387032), a highly efficacious and selective antitumor agent, J. Med. Chem. 47 (2004) 1719-1728;[2] (a) R. Misra, H.Y. Xiao, K. Kim, et al., N-(cycloalkylamino)acyl-2-aminothiazole inhibitors of cyclin-dependent kinase 2. N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl] methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide (BMS-387032), a highly efficacious and selective antitumor agent, J. Med. Chem. 47 (2004) 1719-1728;

  6. [6]

     (b) Y. Koyama, K. Yokose, L. Dolby, et al., Isolation, characterization and synthesis of pimprinine, pimprinethine and pimprinaphine, metabolites of Streptoverticillium olivoreticuli, Agric. Biol. Chem. 45 (1981) 1285-1287.(b) Y. Koyama, K. Yokose, L. Dolby, et al., Isolation, characterization and synthesis of pimprinine, pimprinethine and pimprinaphine, metabolites of Streptoverticillium olivoreticuli, Agric. Biol. Chem. 45 (1981) 1285-1287.

  7. [3] A.O.D. Souza, M.T.C. Pedrosa, J.B. Alderete, et al., Cytotoxicity, antitumoral and antimycobacterial activity of tetrazole and oxadiazole derivatives, Pharmazie 60 (2005) 396-397.[3] A.O.D. Souza, M.T.C. Pedrosa, J.B. Alderete, et al., Cytotoxicity, antitumoral and antimycobacterial activity of tetrazole and oxadiazole derivatives, Pharmazie 60 (2005) 396-397.

  8. [4] K. Atul, A. Pervez, M.A. Ram, et al., Novel 2-aryl-naphtho[1,2-d]oxazole derivatives as potential PTP-1B inhibitors showing antihyperglycemic activities, Eur. J. Med. Chem. 44 (2009) 109-116.[4] K. Atul, A. Pervez, M.A. Ram, et al., Novel 2-aryl-naphtho[1,2-d]oxazole derivatives as potential PTP-1B inhibitors showing antihyperglycemic activities, Eur. J. Med. Chem. 44 (2009) 109-116.

  9. [5] L.S. Boulos, M.H.N. Arsanious, E.F. Ewies, Studies on phosphonium Ylides XXV: the behavior of active phosphacumulene and stabilized alkylidenephosphoranes towards 5-(4H)-oxazolones, Phosphorus Sulfur Silicon Relat. Elem. 184 (2009) 275-290.[5] L.S. Boulos, M.H.N. Arsanious, E.F. Ewies, Studies on phosphonium Ylides XXV: the behavior of active phosphacumulene and stabilized alkylidenephosphoranes towards 5-(4H)-oxazolones, Phosphorus Sulfur Silicon Relat. Elem. 184 (2009) 275-290.

  10. [6] M. Natesan, Z. Gu, P. Stein, Biphenylsulfonamide endothelin receptor antagonists. 2. Discovery of 4'-oxazolyl biphenylsulfonamides as a new class of potent, highly selective ETA antagonists, J. Med. Chem. 43 (2000) 3111-3117.[6] M. Natesan, Z. Gu, P. Stein, Biphenylsulfonamide endothelin receptor antagonists. 2. Discovery of 4'-oxazolyl biphenylsulfonamides as a new class of potent, highly selective ETA antagonists, J. Med. Chem. 43 (2000) 3111-3117.

  11. [7] W.S. Yang, K. Shimada, D. Delva, et al., Identification of simple compounds with microtubule-binding activity that inhibit cancer cell growth with high potency, ACS Med. Chem. Lett. 3 (2012) 35-38.[7] W.S. Yang, K. Shimada, D. Delva, et al., Identification of simple compounds with microtubule-binding activity that inhibit cancer cell growth with high potency, ACS Med. Chem. Lett. 3 (2012) 35-38.

  12. [8] I. Cano, E. Álvarez, M.C. Nicasio, et al., Regioselective formation of 2,5-disubstituted oxazoles via copper(i)-catalyzed cycloaddition of acyl azides and 1-alkynes, J. Am. Chem. Soc. 133 (2011) 191-193.[8] I. Cano, E. Álvarez, M.C. Nicasio, et al., Regioselective formation of 2,5-disubstituted oxazoles via copper(i)-catalyzed cycloaddition of acyl azides and 1-alkynes, J. Am. Chem. Soc. 133 (2011) 191-193.

  13. [9] E.E. Wiegand, D.W. Rathburn, Polyphosphoric acid cyclization of acetamidoketones to 2,5-dimethyl-1,3-oxazoles, Synthesis 2 (1970) 648-649.[9] E.E. Wiegand, D.W. Rathburn, Polyphosphoric acid cyclization of acetamidoketones to 2,5-dimethyl-1,3-oxazoles, Synthesis 2 (1970) 648-649.

  14. [10] (a) A.S.K. Hashmi, Gold-catalyzed organic reactions, Chem. Rev. 107 (2007) 3180-3211;[10] (a) A.S.K. Hashmi, Gold-catalyzed organic reactions, Chem. Rev. 107 (2007) 3180-3211;

  15. [15]

      (b) A. Corma, A. Leyva-Perez, M. Sabater, et al., Gold-catalyzed carbon-heteroatom bond-forming reactions, Chem. Rev. 111 (2011) 1657-1712;(b) A. Corma, A. Leyva-Perez, M. Sabater, et al., Gold-catalyzed carbon-heteroatom bond-forming reactions, Chem. Rev. 111 (2011) 1657-1712;

  16. [16]

      (c) A.S.K. Hashmi, C. Hubbert, Gold and organocatalysis combined, Angew. Chem. Int. Ed. 49 (2010) 1010-1012;(c) A.S.K. Hashmi, C. Hubbert, Gold and organocatalysis combined, Angew. Chem. Int. Ed. 49 (2010) 1010-1012;

  17. [17]

      (d) B. Alcaide, P. Almendros, J. Alonso, Gold catalyzed oxycyclizations of alkynols and alkyndiols, Org. Biomol. Chem. 9 (2011) 4405-4416.(d) B. Alcaide, P. Almendros, J. Alonso, Gold catalyzed oxycyclizations of alkynols and alkyndiols, Org. Biomol. Chem. 9 (2011) 4405-4416.

  18. [11] (a) J. Xiao, X.W. Li, Gold a-oxo carbenoids in catalysis: catalytic oxygen-atom transfer to alkynes, Angew. Chem. Int. Ed. 50 (2011) 7226-7236;[11] (a) J. Xiao, X.W. Li, Gold a-oxo carbenoids in catalysis: catalytic oxygen-atom transfer to alkynes, Angew. Chem. Int. Ed. 50 (2011) 7226-7236;

  19. [19]

      (b) B. Lu, C.Q. Li, L.M. Zhang, Gold-catalyzed highly regioselective oxidation of C- C triple bonds without acid additives: propargyl moieties as masked a,b-unsaturated carbonyls, J. Am. Chem. Soc. 132 (2010) 14070-14072;(b) B. Lu, C.Q. Li, L.M. Zhang, Gold-catalyzed highly regioselective oxidation of C- C triple bonds without acid additives: propargyl moieties as masked a,b-unsaturated carbonyls, J. Am. Chem. Soc. 132 (2010) 14070-14072;

  20. [20]

      (c) L.W. Ye, W.M. He, L.M. Zhang, A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes, Angew. Chem. Int. Ed. 50 (2011) 3236-3239.(c) L.W. Ye, W.M. He, L.M. Zhang, A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes, Angew. Chem. Int. Ed. 50 (2011) 3236-3239.

  21. [12] W.M. He, C.Q. Li, L.M. Zhang, An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation, J. Am. Chem. Soc. 133 (2011) 8482-8485.[12] W.M. He, C.Q. Li, L.M. Zhang, An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation, J. Am. Chem. Soc. 133 (2011) 8482-8485.

  22. [13] (a) T. Sakamoto, M. Shiraiwa, Y. Konodo, et al., A facile synthesis of ethynylsubstituted six-membered n-heteroaromatic compounds, Synthesis (1983) 312- 314;[13] (a) T. Sakamoto, M. Shiraiwa, Y. Konodo, et al., A facile synthesis of ethynylsubstituted six-membered n-heteroaromatic compounds, Synthesis (1983) 312- 314;

  23. [23]

      (b) A. Gangjee, J. Yu, R. Kisliuk, 2-Amino-4-oxo-6-substituted-pyrrolo[2,3-d]pynmidines as potential inhibitors of thymidylate synthase, J. Heterocyclic Chem. 39 (2002) 833-840;(b) A. Gangjee, J. Yu, R. Kisliuk, 2-Amino-4-oxo-6-substituted-pyrrolo[2,3-d]pynmidines as potential inhibitors of thymidylate synthase, J. Heterocyclic Chem. 39 (2002) 833-840;

  24. [24]

      (c) J.J. Qi, C.H. Tung, Development of benzothiazole ‘click-on' fluorogenic dyes, Bioorg. Med. Chem. Lett. 21 (2011) 320-323.(c) J.J. Qi, C.H. Tung, Development of benzothiazole ‘click-on' fluorogenic dyes, Bioorg. Med. Chem. Lett. 21 (2011) 320-323.

  25. [14] (a) M. Rosenblum, N. Brawn, J. Papenmeier, et al., Synthesis of ferrocenylacetylenes, J. Organometal. Chem. 6 (1966) 173-180;[14] (a) M. Rosenblum, N. Brawn, J. Papenmeier, et al., Synthesis of ferrocenylacetylenes, J. Organometal. Chem. 6 (1966) 173-180;

  26. [26]

      (b) A. Aguilar, A. Allen, E. Cabrera, et al., Ferrocenylketene and ferrocenyl-1,2- bisketenes: δirect observation and reactivity measurements, J. Org. Chem. 70 (2005) 9556-9561.(b) A. Aguilar, A. Allen, E. Cabrera, et al., Ferrocenylketene and ferrocenyl-1,2- bisketenes: δirect observation and reactivity measurements, J. Org. Chem. 70 (2005) 9556-9561.

  27. [15] Spectroscopic data: 1a: ¹H NMR (400 MHz, CDCl₃): δ 2.52 (s, 3H), 7.20 (s, 1H), 7.30 (t, 1H, J = 7.6 Hz), 7.40 (t, 2H, J = 7.6 Hz), 7.60 (d, 2H, J = 7.2 Hz). HRMS-EI: [M⁺] Calcd. for C₁₀H₉NO 159.0679, Found 159.0680. 1b: ¹H NMR (400 MHz, CDCl₃): δ 2.58 (s, 3H), 7.33 (s, 1H), 7.49 (m, 2H), 7.66 (d, 1H, J = 7.2 Hz), 7.72 (d, 2H, J = 7.2 Hz), 7.87 (d, 1H, J = 7.6 Hz), 8.09 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₄H₁₁NO 209.0836, Found 209.0838. 1c: ¹H NMR (400 MHz, CDCl₃): δ 2.55 (s, 3H), 7.30 (s, 1H), 7.32-7.36 (m, 1H), 7.87 (d, 1H, J = 8.0 Hz), 8.53 (d, 1H, J = 6.8 Hz), 8.87 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₉H₈N₂O 160.0632, Found 160.0633. 1d: ¹H NMR (400 MHz, CDCl₃): δ 2.59 (s, 3H), 7.42 (s, 1H), 7.57 (t, 1H, J = 8.8 Hz), 7.671 (t, 1H, J = 8.2 Hz), 7.85 (d, 1H, J = 8.4 Hz), 8.10 (d, 1H, J = 8.4 Hz), 8.31 (s, 1H), 9.14 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₃H₁₀N₂O 210.0788, Found 210.0789. 1e: ¹H NMR (400 MHz, CDCl₃): δ 2.50 (s, 3H), 7.05 (s, 1H), 7.25-7.27 (m, 1H), 7.35-7.37 (m, 1H), 7.46-7.47 (m, 1H). HRMS-EI: [M⁺] Calcd. for C₈H₇NOS 165.0243, Found 165.0242. 1f: ¹H NMR (400 MHz, CDCl₃): δ 2.51 (s, 3H), 7.32 (s, 1H), 7.40-7.44 (m, 1H), 7.46-7.50 (m, 1H), 7.69 (s, 1H), 7.90 (d, 1H, J = 9.6 Hz), 8.05 (d, 1H, J = 8.0 Hz). HRMS-EI: [M⁺] Calcd. for C₁₂H₉NOS 215.0400, Found 215.0401. 1g: ¹H NMR (400 MHz, CDCl₃): δ 2.50 (s, 3H), 7.29 (s, 1H), 7.43-7.61 (m, 2H), 7.86 (d, 1H, J = 7.8 Hz), 8.03 (d, 1H, J = 7.4 Hz). HRMS-EI: [M⁺] Calcd. for C₁₁H₈N₂OS 216.0352, Found 216.0351. 1h: ¹HNMR(400 MHz, CDCl₃): δ 2.48 (s, 3H), 4.12 (s, 5H), 4.30 (s, 2H), 4.56 (s, 2H), 6.82 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₄H₁₃FeNO 267.0342, Found 267.0344. Procedure to synthesis of 1i: A solution of NaOH (1.0 mol/L, 3 mL) was added to a stirring solution of 2-methyl-5-(1-tosyl-1H-indol-3-yl)oxazole 6 (106 mg, 0.3 mmol) in 5 mL of methanol and heated to reflux at 80℃ under nitrogen overnight until starting material was consumed as monitored by TLC. Methanol was removed in vacuo and product was extracted with ether (3×20 mL), washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give 56 mg (95% yield) of a yellow solid. ¹H NMR (400 MHz, CDCl₃): δ 2.58 (s, 3H), 7.16 (s, 1H), 7.22-7.32 (m, 2H), 7.46 (d, 1H, J = 7.6 Hz), 7.52 (d, 1H, J = 7.6 Hz), 7.78 (d, 1H, J = 8.0 Hz), 8.38 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₂H₁₀N₂O 198.0788, Found 198.0790.[15] Spectroscopic data: 1a: ¹H NMR (400 MHz, CDCl₃): δ 2.52 (s, 3H), 7.20 (s, 1H), 7.30 (t, 1H, J = 7.6 Hz), 7.40 (t, 2H, J = 7.6 Hz), 7.60 (d, 2H, J = 7.2 Hz). HRMS-EI: [M⁺] Calcd. for C₁₀H₉NO 159.0679, Found 159.0680. 1b: ¹H NMR (400 MHz, CDCl₃): δ 2.58 (s, 3H), 7.33 (s, 1H), 7.49 (m, 2H), 7.66 (d, 1H, J = 7.2 Hz), 7.72 (d, 2H, J = 7.2 Hz), 7.87 (d, 1H, J = 7.6 Hz), 8.09 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₄H₁₁NO 209.0836, Found 209.0838. 1c: ¹H NMR (400 MHz, CDCl₃): δ 2.55 (s, 3H), 7.30 (s, 1H), 7.32-7.36 (m, 1H), 7.87 (d, 1H, J = 8.0 Hz), 8.53 (d, 1H, J = 6.8 Hz), 8.87 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₉H₈N₂O 160.0632, Found 160.0633. 1d: ¹H NMR (400 MHz, CDCl₃): δ 2.59 (s, 3H), 7.42 (s, 1H), 7.57 (t, 1H, J = 8.8 Hz), 7.671 (t, 1H, J = 8.2 Hz), 7.85 (d, 1H, J = 8.4 Hz), 8.10 (d, 1H, J = 8.4 Hz), 8.31 (s, 1H), 9.14 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₃H₁₀N₂O 210.0788, Found 210.0789. 1e: ¹H NMR (400 MHz, CDCl₃): δ 2.50 (s, 3H), 7.05 (s, 1H), 7.25-7.27 (m, 1H), 7.35-7.37 (m, 1H), 7.46-7.47 (m, 1H). HRMS-EI: [M⁺] Calcd. for C₈H₇NOS 165.0243, Found 165.0242. 1f: ¹H NMR (400 MHz, CDCl₃): δ 2.51 (s, 3H), 7.32 (s, 1H), 7.40-7.44 (m, 1H), 7.46-7.50 (m, 1H), 7.69 (s, 1H), 7.90 (d, 1H, J = 9.6 Hz), 8.05 (d, 1H, J = 8.0 Hz). HRMS-EI: [M⁺] Calcd. for C₁₂H₉NOS 215.0400, Found 215.0401. 1g: ¹H NMR (400 MHz, CDCl₃): δ 2.50 (s, 3H), 7.29 (s, 1H), 7.43-7.61 (m, 2H), 7.86 (d, 1H, J = 7.8 Hz), 8.03 (d, 1H, J = 7.4 Hz). HRMS-EI: [M⁺] Calcd. for C₁₁H₈N₂OS 216.0352, Found 216.0351. 1h: ¹HNMR(400 MHz, CDCl₃): δ 2.48 (s, 3H), 4.12 (s, 5H), 4.30 (s, 2H), 4.56 (s, 2H), 6.82 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₄H₁₃FeNO 267.0342, Found 267.0344. Procedure to synthesis of 1i: A solution of NaOH (1.0 mol/L, 3 mL) was added to a stirring solution of 2-methyl-5-(1-tosyl-1H-indol-3-yl)oxazole 6 (106 mg, 0.3 mmol) in 5 mL of methanol and heated to reflux at 80℃ under nitrogen overnight until starting material was consumed as monitored by TLC. Methanol was removed in vacuo and product was extracted with ether (3×20 mL), washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give 56 mg (95% yield) of a yellow solid. ¹H NMR (400 MHz, CDCl₃): δ 2.58 (s, 3H), 7.16 (s, 1H), 7.22-7.32 (m, 2H), 7.46 (d, 1H, J = 7.6 Hz), 7.52 (d, 1H, J = 7.6 Hz), 7.78 (d, 1H, J = 8.0 Hz), 8.38 (s, 1H). HRMS-EI: [M⁺] Calcd. for C₁₂H₁₀N₂O 198.0788, Found 198.0790.

  28. [16] D.J. Gorin, B.D. Sherry, F.D. Toste, Ligand effects in homogeneous Au catalysis, Chem. Rev. 108 (2008) 3351-3378.[16] D.J. Gorin, B.D. Sherry, F.D. Toste, Ligand effects in homogeneous Au catalysis, Chem. Rev. 108 (2008) 3351-3378.

  29. [17] (a) M. Patra, G. Gasser, N. Metzler-Nolte, Small organometallic compounds as antibacterial agents, Dalton Trans. 41 (2012) 6350-6358;[17] (a) M. Patra, G. Gasser, N. Metzler-Nolte, Small organometallic compounds as antibacterial agents, Dalton Trans. 41 (2012) 6350-6358;

  30. [30]

      (b) R.D. Miao, J. Wei, M.H. Lv, et al., Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway, Eur. J. Med. Chem. 46 (2011) 5000-5009;(b) R.D. Miao, J. Wei, M.H. Lv, et al., Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway, Eur. J. Med. Chem. 46 (2011) 5000-5009;

  31. [31]

      (c) B.H. Long, C.L. He, Y.B. Yang, et al., Synthesis, characterization and antibacterial activities of some new ferrocene-containing penems, Eur. J. Med. Chem. 45 (2010) 1181-1188;(c) B.H. Long, C.L. He, Y.B. Yang, et al., Synthesis, characterization and antibacterial activities of some new ferrocene-containing penems, Eur. J. Med. Chem. 45 (2010) 1181-1188;

  32. [32]

      (d) B.H. Long, S.Z. Liang, D.C. Xin, et al., Synthesis, characterization and in vitro antiproliferative activities of new 13-cis-retinoyl ferrocene derivatives, Eur. J. Med. Chem. 44 (2009) 2572-2576;(d) B.H. Long, S.Z. Liang, D.C. Xin, et al., Synthesis, characterization and in vitro antiproliferative activities of new 13-cis-retinoyl ferrocene derivatives, Eur. J. Med. Chem. 44 (2009) 2572-2576;

  33. [33]

      (e) S.L. Shen, J. Zhu, M. Li, et al., Synthesis of ferrocenyl pyrazole-containing chiral aminoethanol derivatives and their inhibition against A549 and H322 lung cancer cells, Eur. J. Med. Chem. 54 (2012) 287-294.(e) S.L. Shen, J. Zhu, M. Li, et al., Synthesis of ferrocenyl pyrazole-containing chiral aminoethanol derivatives and their inhibition against A549 and H322 lung cancer cells, Eur. J. Med. Chem. 54 (2012) 287-294.

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