Notes

One-Pot Synthesis of 5-Aryl Diketo-1H-tetrazol Using 1-Methyl-1-methoxyethyl as Protective Group

  • Liu Mingming ,
  • Zhong Dongwei ,
  • Zhou Jiayi ,
  • Zhou Lu ,
  • Ye Deyong
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  • Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203

Received date: 2011-12-11

  Revised date: 2012-03-06

  Online published: 2012-04-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20902013, 30973641).

Abstract

One-pot reaction was reported for the synthesis of 5-aryl diketo-1H-tetrazols (2). Meanwhile, 1-methyl-1- methoxyethyl (MME) as protective group of tetrazole was firstly reported. The protective and deprotective reactions were performed in moderate conditions and the new method leads to simplified process and increased productivity. Six novel 5-aryl diketo-1H-tetrazol compounds were synthesized by using this method for further biological screening.

Cite this article

Liu Mingming , Zhong Dongwei , Zhou Jiayi , Zhou Lu , Ye Deyong . One-Pot Synthesis of 5-Aryl Diketo-1H-tetrazol Using 1-Methyl-1-methoxyethyl as Protective Group[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1543 -1546 . DOI: 10.6023/cjoc1112111

References

[1] Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379.

[2] Pais, G. C. G.; Zhang, X.; Marchand, C.; Neamati, N.; Cowansage, K.; Svarovskaia, E. S.; Pathak, V. K.; Tang, Y.; Nicklaus, M.; Pommier, Y.; Burke, T. R. J. Med. Chem. 2002, 45, 3184.

[3] Liu, S.; Zeng, L.-F.; Wu, L.; Yu, X.; Xue, T.; Gunawan, A. M.; Long, Y.-Q.; Zhang, Z.-Y. J. Am. Chem. Soc. 2008, 130, 17075.

[4] Summa, V.; Petrocchi, A.; Pace, P.; Matassa, V. G.; Francesco, R. D.; Altamura, S.; Tomei, L.; Koch, U.; Neuner, P. J. Med. Chem. 2004, 47, 14.

[5] Tumey, L. N.; Huck, B.; Gleason, E.; Wang, J.; Silver, D.; Brunden, K.; Boozer, S.; Rundlett, S.; Sherf, B.; Murphy, S.; Bailey, A.; Dent, T.; Leventhal, C.; Harrington, J.; Bennani, Y. L. Bioorg. Med. Chem. Lett. 2004, 14, 4915.

[6] Goldgur, Y.; Craigie, R.; Cohen, G. H.; Fujiwara, T.; Yoshinaga, T.; Fujishita, T.; Sugimoto, H.; Endo, T.; Murai, H.; Davies, D. R. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 13040.

[7] Klaubert, D. H.; Sellstedt, J. H.; Guinosso, C. J.; Bell, S. C.; Capetola, R. J. J. Med. Chem. 1981, 24, 748.

[8] Matsumoto, Y.; Mita, K.; Hashimoto, K. Tetrahedron 1996, 52, 9387.

[9] Kluge, A. F.; Untch, K. G.; Fried, J. H. J. Am. Chem. Soc. 1972, 94, 7827.
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