Abstract
A zirconium(IV) complex of a bidentate Schiff base (ZrL2Cl2) has been synthesized by the reaction of (z)-N-benzylidene-2-hydroxypropane-1-amine (HL) and ZrCl4. Spectroscopic data and elemental analyses are consistent with a monomeric complex with a ligand:Zr ratio of 2:1. The catalytic activity of ZrL2Cl2 has been investigated for the efficient synthesis of a wide variety of quinoxaline derivatives under mild conditions. The employment of ethanol as an environmentally benign solvent in this high yield method, along with high turnover numbers and reusability of the catalyst providing ready scalability, makes it appropriate for practical applications.
Similar content being viewed by others
References
Kim YB, Kim YH, Park JY, Kim SK (2004) Bioorg Med Chem Lett 14:541–544
Brock ED, Lewis DM, Yousaf TI, Harper HH (1999) The Procter and Gamble Company USA, WO 9951688
Dailey S, Feast WJ, Peace RJ, Sage IC, Till S, Wood EL (2001) J Mater Chem 11:2238–2243
Santra BK, Reddy PAN, Neelakanta G, Mahadevan S, Nethaji M, Chakravarty ARJ (2002) Inorg Biochem 89:191–196
Thomas AM, Nethaji M, Mahadevan S, Chakravarty ARJ (2003) Inorg Biochem 94:171–178
Toshima K, Takano R, Ozawa T, Matsumara S (2002) Chem Commun 3:212–213
Kim SY, Park KH, Chung YK (2005) Chem Commun 10:1321–1323
Saka G, Makino K (1988) Heterocycles 27:2481–2515
Huheey JE (1990) Inorganic chemistry: principles of structure and reactivity, 3rd edn, Harper & Row, Singapore, Chap 7
Annunziata L, Pappalardo D, Tedesco C, Pellecchia C (2009) Organometallics 28:688–697
Gorski T, Matusevicha A, Parzuchowski P, Łuciukb I, Malinowskaa Eb (2010) Anal Chim Acta 665:39–46
Blay G, Ferna’ndez I, Pedro JR, Vila C (2007) Org Lett 9:2601–2604
Xu Zh, Ma X, Ma Y, Wang Q, Zhou J (2009) Catal Commun 10:1261–1266
Chen Q, Huang J, Yu J (2005) Inorg Chem Commun 8:444–448
Yeori A, Gendler Sh, Groysman S, Goldberg I, Kol M (2004) Inorg Chem Commun 7:280–282
Gorski Ł, Saniewska A, Parzuchowski P, Meyerhoff ME, Mali E (2005) Anal Chim Acta 551:37–44
Jafarpour M, Rezaeifard A, Aliabadi M (2009) Lett Org Chem 6:94–99
Jafarpour M, Rezaeifard A, Golshani T (2009) J Heterocycl Chem 46:535–539
Jafarpour M, Rezaeifard A, Aliabadi M (2010) Helv Chim Acta 93:405–413
Jafarpour M, Rezaeifard A, Golshani T (2011) Phosphorus Sulfur Silicon 186:140–148
Jafarpour M, Rezaeifard A, Aliabadi M (2009) Appl Catal A General 358:49–53
Jafarpour M, Rezaeifard A, Danehchin M (2011) Appl Catal A General 394:48–51
Jafarpour M, Rezaeifard A, Heidari M (2011) Phosphorus Sulfur Silicon 186:1–13
Jafarpour M, Rezaeifard A, Heidari M (2011) Lett Org Chem 8:202–209
Firouzabadi H, Jafarpour M (2008) J Iran Chem Soc 5:159–183
Jafarpour M, Rezaeifard A, Gazkar S (2011) Trans Met Chem 36:685–690
Aghapoor K, Darabi HR, Mohsenzadeh F, Balavar Y, Daneshyar H (2010) Transition Met Chem 35:49–53
Hasaninejada A, Zare A, Zolfigol MA, Shekouhy M (2009) Synth Commun 39:569–579
Sharma RK, Sharma Ch (2011) Catal Commun 12:327–331
Heravi MM, Taheri Sh, Bakhtiari Kh, Oskooie HA (2007) Catal Commun 8:211–214
Heravi MM, Tehrani MH, Bakhtiari Kh, Oskooie HA (2007) Catal Commun 8:1341–1344
Huang TK, Wang R, Shi L, Lu XX (2008) Catal Commun 9:1143–1147
Potewar TM, Ingale SA, Srinvasan KV (2008) Synth Commun 38:3601–3612
Acknowledgments
Support for this work by Research Council of University of Birjand is highly appreciated.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Jafarpour, M., Rezaeifard, A., Haddad, R. et al. A reusable zirconium(IV) Schiff base complex catalyzes highly efficient synthesis of quinoxalines under mild conditions. Transition Met Chem 38, 31–36 (2013). https://doi.org/10.1007/s11243-012-9657-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-012-9657-5