One-pot synthesis of 1,5-diaza-2,6-cyclooctadiene-3,7-dicarboxylates through a multiple-component reaction

Abstract

Methyl propiolate, formaldehyde, and various acyclic amines were assembled in one-pot into a series of 1,5-diaza-2,6-cyclooctadiene-3,7-dicarboxylates in moderate to good yields. This multiple-component reaction benefits from operational simplicity as well as good material economy.

Keywords

Multiple-component reaction / Methyl propiolate / 1,5-Diaza-2,6-cyclooctadiene-3,7-dicarboxylate

References

[1] Wang W, Domling A. J. Comb. Chem., 2009, 11: 403.

[2] Armstrong R W, Combs A P, Tempest P A, Brown S D, Keating T A. Acc. Chem. Res., 1996, 29: 123.

[3] Hulme C, Gore V. Curr. Med. Chem., 2003, 10: 51.

[4] Simon C, Constantieux T, Rodriguez J. Eur. J. Org. Chem., 2004, 4957.

[5] Stanovnik B. Progress in Heterocyclic Chemistry, 1993, 5: 34.

[6] Frantz D E, Fassler R, Carreira E M. J. Am. Chem. Soc., 2000, 122: 1806.

[7] Wei C, Li C J. J. Am. Chem. Soc., 2002, 124: 5638.

[8] Varela J A, Saa C. Chem. Rev., 2003, 103: 3787.

[9] Attanasi O A, Favi G, Filippone P, Mantellini F, Moscatelli G, Perrulli F R. Org. Lett., 2010, 12: 468.

[10] Seki H, Georg G I. Org. Lett., 2011, 13: 2147.

[11] Liu Y, Zhen W, Dai W, Wang F, Li X. Org. Lett., 2013, 15: 874.

[12] Hiroya K, Matsumoto S, Sakamoto T. Org. Lett., 2004, 6: 2953.

[13] Zhang M, Jiang H, Liu H, Zhu Q. Org. Lett., 2007, 9: 4111.

[14] Ohta Y, Chiba H, Oishi S, Fujii N, Ohno H. J. Org. Chem., 2009, 74: 7052.

[15] Trost B M, Lumb J P, Azzarelli J M. J. Am. Chem. Soc., 2011, 133: 740.

[16] Suresh R, Muthusubramanian S, Senthilkumaran R, Manickam G. J. Org. Chem., 2012, 77: 1468.

[17] Banwell M G, Crasto C F, Easton C J, Karoli T, March D R, Nairn M R, O’Hanlon P J, Oldham M D, Willis A C, Yue W. Chem. Commun., 2001, 2210.

[18] Sun J, Xia E, Yan C. ACS Comb. Sci., 2011, 13: 421.

[19] Balalaie S, Kowsari E. Monatsh. Chem., 2001, 132: 1551.

[20] Cao H, Wang X, Jiang H, Zhu Q, Zhang M, Liu H. Chem. Eur. J., 2008, 14: 11623.

[21] Zhang M, Jiang H, Liu H, Zhu Q. Org. Lett., 2007, 9: 4111.

[22] Nair V, Bindu S, Sreekumar V, Rath N P. Org. Lett., 2003, 5: 665.

[23] Ma C, Yang Y. Org. Lett., 2005, 7: 1343.

[24] Nair V, Sreekumar V, Bindu S, Suresh E. Org. Lett., 2005, 7: 2297.

[25] Lee P H, Lee K, Kang Y. J. Am. Chem. Soc., 2006, 128: 1139.

[26] Xu X, Cheng D, Li J, Guo H, Yan J. Org. Lett., 2007, 9: 1585.

[27] Ding Q, Wu J. Org. Lett., 2007, 9: 4959.

[28] Galliford C V, Scheidt K A. J. Org. Chem., 2007, 72: 1811.

[29] Barluenga J, Suero M G, Campa R D, Florez J. Angew. Chem. Int. Ed., 2010, 49: 9720.

[30] Ruijter E, Scheffelaar R, Orru R V A. Angew. Chem. Int. Ed., 2011, 50: 6234.

[31] Erver F, Hilt G. Org. Lett., 2012, 14: 1884.