Citation: Peng Guo, Jun-Hai Huang, Qing-Chun Huang, Xu-Hong Qian. Synthesis of novel 1,3-oxazole derivatives with insect growthinhibiting activities[J]. Chinese Chemical Letters, ;2013, 24(11): 957-961. shu

Synthesis of novel 1,3-oxazole derivatives with insect growthinhibiting activities

1.
Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Xu-Hong Qian,
Received Date: 19 May 2013
Available Online: 13 June 2013

Straightforward and direct synthesis of 2-substituted-5-oxazolecarbaldehydes was achieved by treating propargylamides with mercury(Ⅱ) perchlorate as catalyst and ammonium cerium(Ⅳ) nitrate as oxidant agent through intramolecular cyclization. These structurally interesting outcomes benefit to synthesize 2,5-disubstituted-1,3-oxazoles with armyworm growth regulating activities.
- Oxazole,
- Mercury,
- Catalyst,
- Growth inhibiting activity
1. [1]
  [1] J.R. Lewis, Muscarine, oxazole, imidazole, thiazole, and peptide alkaloids, and other miscellaneous alkaloids, Nat. Prod. Rep. 12 (1995) 135-163.
2. [2]
  [2] G. Pattenden, Synthetic studies with natural oxazoles and thiazoles, J. Heterocycl. Chem. 29 (1992) 607-618.
3. [3]
  [3] S. Carmeli, R.E. Moore, G.M.L. Patterson, T.H. Corbett, F.A. Valeriote, Tantazoles, unusual cytotoxic alkaloids from the blue-green alga Scytonema mirabile, J. Am. Chem. Soc. 112 (1990) 8195-8197.
4. [4]
  [4] Y. Kato, N. Fusetani, S. Matsunaga, et al., Bioactive marine metabolites. Part 16. Calyculin A. A novel antitumor metabolite from the marine sponge Discodermia calyx, J. Am. Chem. Soc. 108 (1986) 2780-2781.
5. [5]
  [5] B.A. Anderson, L.M. Becke, R.N. Booher, et al., Application of palladium(0)-catalyzed processes to the synthesis of oxazole-containing partial ergot alkaloids, J. Org. Chem. 62 (1997) 8634-8639.
6. [6]
  [6] D.C. Palmer, S. Venkatraman, Synthesis and reactions of oxazoles, in: D.C. Palmer (Ed.), Oxazoles: Synthesis, Reactions, and Spectroscopy, John Wiley & Sons, Hoboken, NJ, USA, 2003, pp. 1-390.
7. [7]
  [7] E.M. Beccalli, E. Borsini, G. Broggini, G. Palmisano, S. Sottocornola, Intramolecular Pd(Ⅱ)-catalyzed cyclization of propargylamides: straightforward synthesis of 5-oxazolecarbaldehydes, J. Org. Chem. 73 (2008) 4746-4749.
8. [8]
  [8] A. Bacchi, M. Costa, B. Gabriele, G. Pelizzi, G. Salerno, Efficient and general synthesis of 5-(Alkoxycarbonyl)methylene-3-oxazolines by palladium-catalyzed oxidative carbonylation of prop-2-ynylamides, J. Org. Chem. 67 (2002) 4450-4457.
9. [9]
  [9] A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi, F. Marinelli, Preparation of 2,5-disubstituted oxazoles from N-propargylamides, Org. Lett. 3 (2001) 2501-2504.
10. [10]
  [10] J.P. Weyrauch, A.S.K. Hashmi, A. Schuster, et al., Cyclization of propargylic amides: mild access to oxazole derivatives, Chem.-Eur. J. 16 (2010) 956-963.
11. [11]
  [11] D. Aguilar, M. Contel, R. Navarro, T. Soler, E.P. Urriolabeitia, Gold(Ⅲ) iminophosphorane complexes as catalysts in C-C and C-O bond formations, J. Organomet. Chem. 694 (2009) 486-493.
12. [12]
  [12] A.S.K. Hashmi, J.P. Weyrauch, W. Frey, J.W. Bats, Gold catalysis: mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects, Org. Lett. 6 (2004) 4391-4394.
13. [13]
  [13] A.S.K. Hashmi, M.C. Blanco Jaimes, A.M. Schuster, F. Rominger, From propargylic amides to functionalized oxazoles: domino gold catalysis/oxidation by dioxygen, J. Org. Chem. 77 (2012) 6394-6408.
14. [14]
  [14] J. Huang, 1,8-Naphthalimide and rhodamine based probes for cations: design, syntheses and property, East China University of Science and Technology, 2009 (PhD dissertation).
15. [15]
  [15] W. Xu, S. Yang, P. Bhadury, et al., Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors, Pestic. Biochem. Phys. 101 (2011) 6-15.
16. [16]
  [16] J. Suzuki, T. Ishida, Y. Kikuchi, et al., Synthesis and activity of novel acaricidal/insecticidal 2,4-diphenyl-1,3-oxazolines, J. Pestic. Sci. 27 (2002) 1-8.
17. [17]
  [17] W. Shi, X. Qian, R. Zhang, G. Song, Synthesis and quantitative structure-activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles, J. Agric. Food Chem. 49 (2001) 124-130.
18. [18]
  [18] Y. Liu, Z. Cui, B. Liu, et al., Design, synthesis, and herbicidal activities of novel 2-cyanoacrylates containing isoxazole moieties, J. Agric. Food Chem. 58 (2010) 2685-2689.
19. [19]
  [19] F. Grundmann, V. Dill1, A. Dowling, et al., Identification and isolation of insecticidal oxazoles from Pseudomonas spp, Beilstein, J. Org. Chem. 8 (2012) 749-752.
20. [20]
  [20] A.D. Gutman, 1,3-Oxazole phosphates and phosphonates as insecticides and miticides, U.S. Patent 4,137,308 (1979).
21. [21]
  [21] R. Sun, Y. Li, L. Xiong, Y. Liu, Q. Wang, Design, synthesis, and insecticidal evaluation of new benzoylureas containing isoxazoline and isoxazole group, J. Agric. Food Chem. 59 (2011) 4851-4859.
22. [22]
  [22] L. Syper, Partial oxidation of aliphatic side chains with cerium (Ⅳ), Tetrahedron Lett. 7 (1966) 4493-4498.
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沈阳化工大学材料科学与工程学院沈阳 110142