Full Text:   <3649>

CLC number: O621.3

On-line Access: 

Received: 2008-11-17

Revision Accepted: 2009-02-11

Crosschecked: 2009-04-28

Cited: 9

Clicked: 8034

Citations:  Bibtex RefMan EndNote GB/T7714

-   Go to

Article info.
1. Reference List
Open peer comments

Journal of Zhejiang University SCIENCE B 2009 Vol.10 No.6 P.472-478

http://doi.org/10.1631/jzus.B0820366


Facile and efficient one-pot synthesis of 2-arylbenzoxazoles using hydrogen tetrachloroaurate as catalyst under oxygen atmosphere


Author(s):  Yun-kui LIU, Da-jie MAO, Shao-jie LOU, Jian-qiang QIAN, Zhen-yuan XU

Affiliation(s):  State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China

Corresponding email(s):   ykuiliu@zjut.edu.cn, greensyn@zjut.edu.cn

Key Words:  2-Arylbenzoxazoles, 2-Aminophenol, Aldehydes, Hydrogen tetrachloroaurate, One-pot synthesis


Yun-kui LIU, Da-jie MAO, Shao-jie LOU, Jian-qiang QIAN, Zhen-yuan XU. Facile and efficient one-pot synthesis of 2-arylbenzoxazoles using hydrogen tetrachloroaurate as catalyst under oxygen atmosphere[J]. Journal of Zhejiang University Science B, 2009, 10(6): 472-478.

@article{title="Facile and efficient one-pot synthesis of 2-arylbenzoxazoles using hydrogen tetrachloroaurate as catalyst under oxygen atmosphere",
author="Yun-kui LIU, Da-jie MAO, Shao-jie LOU, Jian-qiang QIAN, Zhen-yuan XU",
journal="Journal of Zhejiang University Science B",
volume="10",
number="6",
pages="472-478",
year="2009",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.B0820366"
}

%0 Journal Article
%T Facile and efficient one-pot synthesis of 2-arylbenzoxazoles using hydrogen tetrachloroaurate as catalyst under oxygen atmosphere
%A Yun-kui LIU
%A Da-jie MAO
%A Shao-jie LOU
%A Jian-qiang QIAN
%A Zhen-yuan XU
%J Journal of Zhejiang University SCIENCE B
%V 10
%N 6
%P 472-478
%@ 1673-1581
%D 2009
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.B0820366

TY - JOUR
T1 - Facile and efficient one-pot synthesis of 2-arylbenzoxazoles using hydrogen tetrachloroaurate as catalyst under oxygen atmosphere
A1 - Yun-kui LIU
A1 - Da-jie MAO
A1 - Shao-jie LOU
A1 - Jian-qiang QIAN
A1 - Zhen-yuan XU
J0 - Journal of Zhejiang University Science B
VL - 10
IS - 6
SP - 472
EP - 478
%@ 1673-1581
Y1 - 2009
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.B0820366


Abstract: 
In this paper, we presented a novel method for the facile and efficient one-pot synthesis of 2-Arylbenzoxazoles, which were directly synthesized from 2-Aminophenol and aldehydes catalyzed by hydrogen tetrachloroaurate (HAuCl4·4H2O) under an oxygen atmosphere with anhydrous tetrahydrofuran (THF) as solvent or in solvent-free condition. The results show that this method could bring excellent yields as high as 96%. THF was proven to be the best choice among several solvents screened and the reaction was tolerated with a variety of aromatic aldehydes possessing electron-donating or withdrawing groups. The advantages of the present method lie in catalytic process using economic and environmentally benign dioxygen as oxidant.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

[1] Arcadi, A., 2008. Alternative synthetic methods through new developments in catalysis by gold. Chem. Rev., 108(8): 3266-3325.

[2] Arcadi, A., Giuseppe, S.D., 2004. Recent applications of gold catalysis in organic synthesis. Curr. Org. Chem., 8(9): 795-812.

[3] Boring, E., Geletti, Y.V., Hill, C.J., 2001. A homogeneous catalyst for selective O2 oxidation at ambient temperature. Diversity-based discovery and mechanistic investigation of thioether oxidation by the Au(III)Cl2NO3(thioether)/O2 system. J. Am. Chem. Soc., 123(8):1625-1635.

[4] Bougrin, K., Loupy, A., Soufiaoui, M., 1998. Trois nouvelles voies de synthèse des dérivés 1,3-azoliques sous micro-ondes. Tetrahedron, 54(28):8055-8064

[5] Chang, J., Zhao, K., Pan, S., 2002. Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases—a solution-phase strategy for library synthesis. Tetrahedron Lett., 43(6):951-954.

[6] Choudhary, V.R., Jha, R., Jana, P., 2007. Solvent-free selective oxidation of benzyl alcohol by molecular oxygen over uranium oxide supported nano-gold catalyst for the production of chlorine-free benzaldehyde. Green Chem., 9(3):267-272.

[7] Deluca, M.R., Kerwin, S.M., 1997. The total synthesis of UK-1. Tetrahedron Lett., 38(2):199-202.

[8] de Vos, D.E., Sels, B. F., 2005. Gold redox catalysis for selective oxidation of methane to methanol. Angew. Chem. Int. Ed., 44(1):30-32.

[9] Díaz-Requejo, M.M., Pérez, P.J., 2008. Coinage metal catalyzed C-H bond functionalization of hydrocarbons. Chem. Rev., 108(8):3379-3394.

[10] El′tsov, A.V., 1990. Organic Photochromers. Plenum Press, New York, p.178.

[11] Evindar, G., Batey, R.A., 2006. Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides. J. Org. Chem., 71(5):1802-1808.

[12] Guan, B, Xing, D., Cai, G., Wan, X., Yu, N., Fang, Z., Yang, L., Shi, Z., 2005. Highly selective aerobic oxidation of alcohol catalyzed by a gold(I) complex with an anionic ligand. J. Am. Chem. Soc., 127(51):18004-18005.

[13] Haruta, M., Kobayashi, T., Sano, H., Yamada, N., 1987. Novel gold catalysts for the oxidation of carbon monoxide at a temperature far below 0 °C. Chem. Lett., 16(2):405-408.

[14] Hashmi, A.S.K., 2003. Homogeneous gold catalysts and alkynes: a successful liaison. Gold Bull., 36(1):3-9.

[15] Hashmi, A.S.K., 2004. Homogeneous catalysis by gold. Gold Bull., 37(1-2):51-65.

[16] Hashmi, A.S.K., 2007. Gold-catalyzed organic reactions. Chem. Rev., 107(7):3180-3211.

[17] Hashmi, A.S.K., Hutching, G.J., 2006. Gold catalysis. Angew. Chem. Int. Ed., 45(47):7896-7936.

[18] Heynderickx, A., Guglielmetti, R., Dubest, R., Aubard, J., Samat, A., 2003. Sulfinyl- and sulfonyl-substituted 2-benzylbenzoxazoles and 2-benzylbenzothiazoles as potential photochromic compounds. Synthesis, (7):1112-1116.

[19] Jiménez-Núňez, E., Echavarren, A.M., 2007. Molecular diversity through gold catalysis with alkynes. Chem. Commun., (4):333-346.

[20] Kanaoka, S., Yagi, N., Fukuyama, Y., Aoshima, S., Tsunoyama, H., Tsukuda, T., Sakurai, H., 2007. Thermosensitive gold nanoclusters stabilized by well-defined vinyl ether star polymers: reusable and durable catalysts for aerobic alcohol oxidation. J. Am. Chem. Soc., 129(40): 12060-12061.

[21] Kawashita, Y., Nakamichi, N., Kawabata, H., Hayashi, M., 2003. Direct and practical synthesis of 2-arylbenzoxazoles promoted by activated carbon. Org. Lett., 5(20): 3713-3715.

[22] Kidwai, M., Bansal, V., Saxena, A., Aerry, S., Mozumdar, S., 2006. Cu-nanoparticles: efficient catalysts for the oxidative cyclization of Schiffs’ bases. Tetrahedron Lett., 47(46):8049-8053.

[23] Lazar, M., Angelici, R.J., 2006. Gold metal-catalyzed reactions of isocyanides with primary amines and oxygen: analogies with reactions of isocyanides in transition metal complexes. J. Am. Chem. Soc., 128(32):10613-10620.

[24] Lewis, J.C., Wiedemann, S.H., Bergman, R.G., Ellman, J.A., 2004. Arylation of heterocycles via rhodium-catalyzed C-H bond functionalization. Org. Lett., 6(1):35-38.

[25] Li, H., Guan, B., Wang, W., Xing, D., Fang, Z., Wan, X., Yang, L., Shi, Z., 2007. Aerobic oxidation of alcohol in aqueous solution catalyzed by gold. Tetrahedron, 63(35):8430-8434.

[26] Li, Z., Brouwer, C., He, C., 2008. Gold-catalyzed organic transformations. Chem. Rev., 108(8):3239-3265.

[27] Liu, Y., Song, F., Guo, S., 2006. Cleavage of a carbon-carbon triple bond via gold-catalyzed cascade cyclization/ oxidative cleavage reactions of (Z)-enynols with molecular oxygen. J. Am. Chem. Soc., 128(35):11332-11333.

[28] Mallat, T., Baiker, A., 2004. Oxidation of alcohols with molecular oxygen on solid catalysts. Chem. Rev., 104(6): 3037-3058.

[29] Min, B.K., Friend, C.M., 2007. Heterogeneous gold-based catalysis for green chemistry: low-temperature CO oxidation and propene oxidation. Chem. Rev. 107(6): 2709-2724.

[30] Miyamura, H., Matsubara, R., Muyazaki, Y., Kobayashi, S., 2007. Aerobic oxidation of alcohols at room temperature and atmospheric conditions catalyzed by reusable gold nanoclusters stabilized by the benzene rings of polystyrene derivatives. Angew. Chem. Int. Ed., 46(22):4151-4154.

[31] Moghaddam, F.M., Bardajee, G.R., Ismaili, H., Taimoory, S.M.D., 2006. Facile and efficient one-pot protocol for the synthesis of benzoxazole and benzothiazole derivatives using molecular iodine as catalyst. Synth. Commun., 36(17):2543-2548.

[32] Muzart, J., 2008. Gold-catalysed reactions of alcohols: isomerisation, inter- and intramolecular reactions leading to C-C and C-heteroatom bonds. Tetrahedron, 64(25):5815-5849.

[33] Nakagawa, K., Onoue, H., Sugita, J., 1964. Oxidation with nickel peroxide. IV. The preparation of benzoxazoles from Schiff’s Bases. Chem. Pharm. Bull., 12(10): 1135-1138.

[34] Park, K.H., Jun, K., Shin, S.R., Oh, S.W., 1996. 2-arylbenzoxazoles from phenolic Schiff’s bases by thianthrene cation radical. Tetrahedron Lett., 37(49): 8869-8870.

[35] Park, M.S., Jun, K., Shin, S.R., Oh, S.W., Park, K.H., 2002. Synthesis of 2-(2-, 3-, and 4-pyridyl)benzoxazoles by the reaction of phenolic Schiff bases with thianthrene cation radical. J. Heterocycl. Chem., 39(6):1279-1281.

[36] Reiser, A., Leyshon, L.J., Saunders, D., Mijovic, M.V., Bright, A., Bogie, J., 1972. Fluorescence of aromatic benzoxazole derivatives. J. Am. Chem. Soc., 94(7):2414-2421.

[37] Sato, Y., Yamada, M., Yoshida, S., Soneda, T., Ishikawa, M., Nizato, T., Suzuki, K., Konno, F., 1998. Benzoxazole derivatives as novel 5-HT3 receptor partial agonists in the gut. J. Med. Chem., 41(16):3015-3021.

[38] Shen, H.C., 2008. Recent advances in syntheses of carbocycles and heterocycles via homogeneous gold catalysis. Part 2: Cyclizations and cycloadditions. Tetrahedron, 64(34): 7847-7870.

[39] Shul(pin, G.B., Shilov, A.E., Süss-Fink, G., 2001. Alkane oxygenation catalysed by gold complexes. Tetrahedron Lett., 42(41):7253-7256.

[40] Skouta, R., Li, C.J., 2008. Gold-catalyzed reactions of C-H bonds. Tetrahedron, 64(22):4917-4938.

[41] Srivastava, R.G., Venkataramani, P.S., 1988. Barium manganate oxidation in organic synthesis: part III: oxidation of Schiff’s bases to benzimidazoles, benzoxazoles and benzthiazoles. Synth. Commun., 18(13):1537-1544.

[42] Stephens, F.F., Bower, J.D., 1949. The preparation of benzimidazoles and benzoxazoles from Schiff bases. Part I. J. Chem. Soc., 2971-2972.

[43] Tauer, E., Grellmann, K.H., 1981. Photochemical and thermal reactions of aromatic Schiff bases. J. Org. Chem., 46(21): 4252-4258.

[44] Temiz, O., Oren, I., Sener, E., Yalcin, I., Ucarturk, N., 1998. Synthesis and microbiological activity of some novel 5- or 6-methyl-2-(2,4-disubstituted phenyl) benzoxazole derivatives. Il Farmaco, 53(5):337-341.

[45] Terashima, M., Ishii, M., Kanaoka, Y., 1982. A facile synthesis of 2-substituted benzoxazoles. Synthesis, (6):484-485.

[46] Trost, B.M., Flemming, I. (Eds.), 1991. Comprehensive Organic Synthesis. Pergamon Press, New York, p133.

[47] Tsunoyama, H., Sakurai, H., Negishi, Y., Tsukuda, T., 2005. Size-specific catalytic activity of polymer-stabilized gold nanoclusters for aerobic alcohol oxidation in water. J. Am. Chem. Soc., 127(26):9374-9375.

[48] Valden, M., Lai, X., Goodman, D.W., 1998. Onset of catalytic activity of gold clusters on titania with the appearance of nonmetallic properties. Science, 281(5383):1647-1650.

[49] Varma, R.S., Kumar, D., 1998. Manganese triacetate oxidation of phenolic Schiff bases: synthesis of 2-arylbenzoxazoles. J. Heterocycl. Chem., 35(6):1539-1540.

[50] Varma, R.S., Saini, R.K., Prakash, O., 1997. Hypervalent iodine oxidation of phenolic Schiff’s bases: synthesis of 2-arylbenzoxazoles. Tetrahedron Lett., 38(15):2621-2622.

[51] Widenhoefer, R.A., Han, X., 2006. Gold-catalyzed hydroamination of C-C multiple bonds. Eur. J. Org. Chem., (20):4555-4563.

[52] Wilfred, C.D., Taylor, R.K.J., 2004. Preparation of 2-substituted benzimidazoles and related heterocycles directly from activated alcohols using TOP methodology. Synlett, (9):1628-1630.

[53] Xing, D., Guan, B., Cai, G., Fang, Z., Yang, L., Shi, Z., 2006. Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water. Org. Lett., 8(4):693-696.

[54] Xu, D.Q., Yang, W.L., Luo, S.P., Wang, B.T., Wu, M., Xu, Z.Y., 2007. Fischer indole synthesis in brønsted acidic ionic liquids: a green, mild, and regiospecific reaction system. Eur. J. Org. Chem., (6):1007-1012.

[55] Yang, T., Campbell, L., Dixon, D.J., 2007. A Au(I)-catalyzed N-acyl iminium ion cyclization cascade. J. Am. Chem. Soc., 129(40):12070-12071.

[56] Yuan, Y., Bian, Y., 2007. Gold(III) catalyzed oxidation of sulfides to sulfoxides with hydrogen peroxide. Tetrahedron Lett., 48(48):8518-8520.

[57] Zhu, B., Angelici, R.J., 2007. Non-nanogold catalyzed aerobic oxidation of secondary amines to imines. Chem. Commun., (21):2157-2159.

Open peer comments: Debate/Discuss/Question/Opinion

<1>

Please provide your name, email address and a comment





Journal of Zhejiang University-SCIENCE, 38 Zheda Road, Hangzhou 310027, China
Tel: +86-571-87952783; E-mail: cjzhang@zju.edu.cn
Copyright © 2000 - 2024 Journal of Zhejiang University-SCIENCE