Issue

Vol. 25 No. 3 (2013): Vol 25 Issue 3

Copyright (c) 2013 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Pseudo Three-Component Synthesis of 1,3-Dioxol Derivatives from the Reaction Between Isocyanides and Aldehydes in Solventless Conditions

https://doi.org/10.14233/ajchem.2013.13146
Ali Reza Kazemizadeh
Research Laboratory of MCRs, Department of Chemistry, Zanjan Branch, Islamic Azad University, PO Box 49195-467, Zanjan, Iran
Ali Ramazani
Research Laboratory of MCRs, Department of Chemistry, Zanjan Branch, Islamic Azad University, PO Box 49195-467, Zanjan, Iran

Corresponding Author(s) : Ali Reza Kazemizadeh

alirezakazemizadeh@yahoo.com

Asian Journal of Chemistry, Vol. 25 No. 3 (2013): Vol 25 Issue 3

Abstract

Pseudo three-component reaction between isocyanides and aldehydes in a 1:2 ratio in solventless conditions at room temperature led to 1,3-dioxol derivatives in high yields. The reaction proceeds cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their 1H NMR, 13C NMR, mass, IR spectra and elemental analysis.

Keywords

Isocyanide Multicomponent reactions 1,3-Dioxol derivatives Solventless conditions
Reza Kazemizadeh, A., & Ramazani, A. (2012). Pseudo Three-Component Synthesis of 1,3-Dioxol Derivatives from the Reaction Between Isocyanides and Aldehydes in Solventless Conditions. Asian Journal of Chemistry, 25(3), 1558–1560. https://doi.org/10.14233/ajchem.2013.13146
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. P. Vanelle, J. Meuche, J. Maldonado, M.P. Crozet, F. Delmas and P. TimonDavid, Eur. J. Med. Chem., 35, 157 (2000).
  2. A.S. Kalgutkar, B. Feng, H.T. Nguyen, K.S. Frederick, S.D. Campbell, H.L. Hatch, Y.A. Bi, D.C. Kazolias, R.E. Davidson, R.J. Mireles, D.B. Duignan, E.F. Choo and S.X. Zhhao, Drug Metab. Dispos., 35, 2111 (2007).
  3. I. Ohno, K. Hirata, C. Ishida, M. Ihara, K. Matsuda and S. Kagabu, Bioorg. Med. Chem. Lett., 17, 4500 (2007).
  4. A.C.L. Leite, K.P. da Silva, I.A. de Souza, J.M. de Araújo and D.J. Brondani, Eur. J. Med. Chem., 39, 1059 (2004).
  5. N.H. Ouf and A.E. Amr, Monatsh Chem., 139, 579 (2008).
  6. a) J. Zhu, Multicomponent Reactions, WILEY-VCH: Weinheim (2005); b) J. Zhu, Eur. J. Org. Chem., 1133 (2003).
  7. a) A. Dömling and I. Ugi, Angew. Chem. Int. Ed., 39, 3169 (2000); b) A. Dömling, Chem. Rev., 106, 17 (2006).
  8. a) M.A. Mironov, QSAR Comb. Sci., 25, 423 (2006); b) A. Ramazani, M. Rouhani, A. Rezaei, N. Shajari and A. Souldozi, Helv. Chim. Acta, 94, 282 (2011).
  9. a) A. Shaabani, A. Maleki, A.H. Rezayan and A. Sarvary, Mol. Divers., 15, 41 (2011); b) L. Banfi, R. Riva and A. Basso, Synlett., 23 (2010).
  10. a) A. Ramazani, Y. Ahmadi and R. Tarasi, Heteroat. Chem., 22, 79 (2011); b) A. Ramazani, A. Rezaei, A. Tofangchi Mahyari, M. Rouhani and M. Khoobi, Helv. Chim. Acta, 93, 2033 (2010); c) A. Ramazani, A. Tofangchi Mahyari, M. Rouhani and A. Rezaei, Tetrahedron Lett., 50, 5625 (2009).
  11. a) I. Yavari, M.J. Bayat, M. Sirouspour and S. Souri, Tetrahedron, 66, 7995 (2010); b) J. Azizian, A. Ramazani and M. Haji, Helv. Chim. Acta, 94, 371 (2011); c) A.R. Kazemizadeh and A. Ramazani, Arkivoc, 159 (2008).
  12. a) A. Ramazani, Y. Ahmadi, M. Rouhani, N. Shajari and A. Souldozi, Heteroat. Chem., 21, 368 (2010); b) A. Ramazani and A. Rezaei, Org. Lett., 12, 2852 (2010); c) A. Ramazani, N. Shajari, A. Mahyari and Y. Ahmadi, Mol. Divers, 15, 521 (2011).
  13. a) A. Ramazani and A.R. Kazemizadeh, Curr. Org. Chem., 15, 3986 (2011); b) A.R. Kazemizadeh and A. Ramazani, J. Braz. Chem. Soc., 20, 309 (2009); c) M.T. Maghsoodlou, G. Marandi, N. Hazeri, S.M. Habibi Khorassani and A.A. Mirzaei, Mol. Divers, 15, 227 (2011).
  14. a) S. Sadjadi and M.M. Heravi, Tetrahedron, 67, 2707 (2011); b) M.M. Heravi and S. Moghimi, J. Iran. Chem. Soc., 8, 306 (2011).
  15. a) S.M. Shoaei, A.R. Kazemizadeh and A. Ramazani, Chin. J. Struct. Chem., 30, 568 (2011); b) A.R. Kazemizadeh and A. Ramazani, Asian J. Chem., 23, 4613 (2011); A.R. Kazemizadeh and A. Ramazani, Curr. Org. Chem., 16, 418 (2012).
  16. a) A. Ramazani,A. Morsali, B. Ganjeie, A.R. Kazemizadeh, E. Ahmadi, R. Kempe and I.Z. Hertle, Naturforsch, 60b, 569 (2005); b) A. Ramazani, F. Marandi and A.R. Kazemizadeh,Phosphorus, Sulfur, Silicon Rel. Elem., 180, 1541 (2005).
  17. a) A. Ramazani, A.R. Kazemizadeh, B. Ganjeie and E. Ahmadi, Phosphorus, Sulfur, Silicon Rel. Elem., 180, 2569 (2005); b) A. Ramazani, E. Ahmadi, A.R. Kazemizadeh, L. Dolatyari, N. Noshiranzadeh, I. Eskandari and A. Souldozi, Phosphorus, Sulfur, Silicon Rel. Elem., 180, 2419 (2005); c) M. Rahnema, M.R. Bigdeli, A.R. Kazemizadeh and A. Ramazani, Phosphorus, Sulfur, Silicon Rel. Elem., 182, 1683 (2007).
  18. a) B. Ganjeie, A. Ramazani and A.R. Kazemizadeh, Phosphorus, Sulfur, Silicon Rel. Elem., 182, 1703 (2007); b) A. Ramazani, A. Morsali, B. Ganjeie, A.R. Kazemizadeh and E. Ahmadi, Phosphorus, Sulfur, Silicon Rel. Elem., 180, 2439 (2005); c) A. Ramazani, A.R. Kazemizadeh, B. Ganjeie and E. Ahmadi, Asian J. Chem., 17, 2375 (2005).
  19. a) A. Ramazani, E. Ahmadi, B. Ganjeie, A.R. Kazemizadeh and A. Morsali, Asian J. Chem., 17, 2371 (2005); b) A. Ramazani,A. Souldozi, F. Marandi and A.R. Kazemizadeh, Asian J. Chem., 17, 293 (2005).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0