SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 12: 3550 - 3559

DOI: https://doi.org/10.6023/cjoc201905009

Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes

  • Yang Minrong ,
  • Zhu Ya'nan ,
  • Xu Fan
Expand
  • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received date: 2019-05-06

  Revised date: 2019-07-21

  Online published: 2019-08-07

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272168) and the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 18KJA150007).

Fold

Abstract

2,8-Dioxabicyclo[3.3.1]nonane exists in many natural biologically active materials. Cationic aluminum complex[AlCl(CH3CN)5]2+[(AlCl4)2]2-·CH3CN can be easily prepared via the reaction of AlCl3 with CH3CN at room temperature. It served as efficient catalyst for the tandem Friedel-Crafts alkylation/ketalization reaction of 2-hydroxychalcones with naphthols to produce diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes in moderate to high yields. This method provides a practical process to afford this type of biologically important compounds in good yields using easily available and inexpensive catalyst.

Key words： cationic aluminum complex; Lewis acid; catalysis; 2,8-dioxabicyclo[3.3.1]nonane; synthesis

Cite this article

Yang Minrong , Zhu Ya'nan , Xu Fan . Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes[J]. Chinese Journal of Organic Chemistry, 2019 , 39(12) : 3550 -3559 . DOI: 10.6023/cjoc201905009

References

[1] Lou, H. X.; Yamazaki, Y.; Sasaki, T.; Uchida, M.; Tanaka, H.; Oka, S. Phytochemistry 1999, 51, 297.
[2] Xu, X. Y.; Xie, H. H.; Wang, Y. F.; Wei, X. Y. J. Agric. Food Chem. 2010, 58, 11667.
[3] Suedee, A.; Tewtrakul, S.; Panichayupakaranant, P. Pharm Biol. 2013, 51, 1256.
[4] (a) Jurd, L.; Waiss, Jr. A. C. Tetrahedron 1965, 21, 1471.
(b) Pomilio, A.; Müller, O.; Schilling, G.; Weinges, K. Justus Liebigs Ann. Chem. 1977, 597.
(c) Selenski, C.; Pettus, T. R. R. Tetrahedron 2006, 62, 5298.
(d) Kraus, G. A.; Yuan, Y.; Kempema, A. Molecules 2009, 14, 807.
[5] (a) Van Allan, J. A.; Giannini, D. D.; Whitesides, T. H. J. Org. Chem. 1982, 47, 820.
(b) Tunca, A. A.; Talinli, N.; Akar, A. Tetrahedron 1995, 51, 2109.
(c) Banihashemi, A.; Rahmatpour, A. Tetrahedron 1999, 55, 7271.
(d) Rosenau, T.; Potthast, A.; Hofinger, A.; Kosma, P. Angew. Chem. Int. Ed. 2002, 41, 1171.
(e) Talinli, N.; Karliga, B. J. Heterocycl. Chem. 2004, 41, 205.
[6] Mashraqui, S. H.; Patil, M. B.; Mistry, H. D.; Ghadigaonkar, S.; Meetsma, A. Chem. Lett. 2004, 33, 1058.
[7] Wang, F. J.; Chen, F.; Qu, M. L.; Li, T.; Liu, Y. L.; Shi, M. Chem. Commun. 2013, 49, 3360.
[8] Weinges, K.; Theobald, H. Justus Liebigs Ann. Chem. 1971, 743, 203.
[9] Rao, Y.; Yin, G. Org. Biomol. Chem. 2013, 11, 6029.
[10] Jiang, X. L.; Song, Z. L.; Xu, C.; Yao, Q. Z.; Zhang, A. Eur. J. Org. Chem. 2014, 418.
[11] Ganguly, N. C.; Roy, S.; Mondal, P. RSC Adv. 2014, 4, 42078.
[12] Xia, L.; Cai, H.; Lee, Y. R. Org. Biomol. Chem. 2014, 12, 4386.
[13] Samanta, S.; Sepay, N.; Mallik, S.; Mondal, R.; Molla, M. R.; Mallik, A. K. Synth. Commun. 2017, 47, 2195.
[14] Zhu, Y. N.; Yao, Z. G.; Xu, F. Tetrahedron 2018, 74, 4211.
[15] Zhu, X. H.; Li, G. Y.; Xu, F.; Zhang, Y.; Xue, M. Q.; Shen, Q. Tetrahedron 2017, 73, 1451.
[16] CCDC 1568665(3af). The supplementary crystallographic data for this paper can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_re-quest/cif.
[17] (a) Wu, Y. C.; Liu, L.; Liu, Y. L.; Wang, D.; Chen, Y. J. J. Org. Chem. 2007, 72, 9383.
(b) Aoki, S.; Amamoto, C.; Oyamada, J.; Kitamura, T. Tetrahedron 2005, 61, 9291.
Options
Outlines

/

〈 〉