Solvent-free 1,3-dipolar cycloaddition of azomethine imines with terminal alkynes promoted by calcium fluoride under the ball milling condition

Xianglong Chen , Chunman Jia , Li Cao , Dela Zhang , Shuixiang Liu , Qi Zhang

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (4) : 543 -548.

PDF
Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (4) : 543 -548. DOI: 10.1007/s40242-015-4480-0
Article

Solvent-free 1,3-dipolar cycloaddition of azomethine imines with terminal alkynes promoted by calcium fluoride under the ball milling condition

Author information +
History +
PDF

Abstract

A convenient and efficient procedure for the synthesis of N,N-bicyclic pyrazolidinone derivatives has been developed via the reaction of azomethine imines with terminal alkynes under the ball milling condition without solvent, which was promoted by calcium fluoride with a catalyst of copper(I) salt. The cyclization reactions exhibited moderate to high yields.

Keywords

Ball-milling / 1,3-Dipolar cycloaddition / Click chemistry / Solvent-free reaction

Cite this article

Download citation ▾
Xianglong Chen, Chunman Jia, Li Cao, Dela Zhang, Shuixiang Liu, Qi Zhang. Solvent-free 1,3-dipolar cycloaddition of azomethine imines with terminal alkynes promoted by calcium fluoride under the ball milling condition. Chemical Research in Chinese Universities, 2015, 31(4): 543-548 DOI:10.1007/s40242-015-4480-0

登录浏览全文

4963

注册一个新账户 忘记密码

References

[1]

Eicher T, Hauptmann S. The Chemistry of Heterocycles, 2003 2nd Ed. Weinheim: Wiley-VCH.

[2]

Varvounis G, Fiamegos Y, Pilidis G. Adv. Heterocycl. Chem., 2001, 80: 73.

[3]

Elguero J.; Eds.: Katritzky A. R., Rees C. W., Scriven E. F. V., Pyrazoles: Comprehensive Heterocyclic Chemistry II, Vol. 3, Elsevier, Oxford, 1996,1

[4]

Radl S.; Eds.: Katritzky A. R., Rees C. W., Scriven E. F. V., Bicyclic Systems with Two Ring Junction Nitrogen Atom: Comprehensive Heterocyclic Chemistry II, Vol. 8, Elsevier, Oxford, 1996, 747

[5]

Konaklieva M I, Plotlin B J. Curr. Med. Chem. Anti-infect. Agents, 2003, 2: 287.

[6]

Hanessian S, McNaughton-Smith G, Lombart H G, Lubell W D. Tetrahedron, 1997, 53: 12789.

[7]

Marchand-Brynaert J., Ghosez L.; Eds.: Lukacs G., Ohno M., Recent Progress in the Chemical Synthesis of Antibiotics, Springer, Berlin, 1990

[8]

Jungheim L N, Sigmund S K. J., Org. Chem., 1987, 52: 4007.

[9]

Ternansky R J, Draheim S E, Pike A J, Counter F T, Eudaly J A, Kasher J S. J. Med. Chem., 1993, 36: 3224.

[10]

Nakano H, Tsugawa N, Takahashi K, Okuyama Y, Fujita R. Tetrahedron, 2006, 62: 10879.

[11]

Sibi M P, Soeta T. J. Am. Chem. Soc., 2007, 129: 4522.

[12]

Huisgen R.; Ed.: Padwa A., 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984, 1

[13]

Jiang Y, Han Q, Shen R, Wang B. Chem. Res. Chinese Universities, 2014, 30(5): 755.

[14]

Padwa A, Pearson W H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 2003, New York: Wiley.

[15]

Dorn H, Otto A. Chem. Ber., 1968, 101: 3287.

[16]

Dorn H, Otto A. Angew. Chem., 1968, 80: 196.

[17]

Shintani R, Fu G C. J. Am. Chem. Soc., 2003, 125: 10778.

[18]

Suarez A, Downey C W, Fu G C. J. Am. Chem. Soc., 2005, 127: 11244.

[19]

Keller M, Sido A S S, Pale P. Chem. Eur. J., 2009, 15: 2810.

[20]

Yoshimura K, Oishi T, Yamaguchi K, Mizuno N. Chem. Eur. J., 2011, 17: 3827.

[21]

Arai T, Ogino Y, Sat T. Chem. Commun., 2013, 49: 7776.

[22]

Arai T, Ogin Y. Molecules, 2012, 17: 6170.

[23]

Shao C, Zhang Q, Cheng G, Cheng C, Wang X. Eur. J. Org. Chem., 2013, 28: 6443.

[24]

Imaizumi T, Yamashita Y, Kobayashi S. J. Am. Chem. Soc., 2012, 134: 20049.

[25]

McNaught A D, Wilkinson A. IUPAC. In Compendium of Chemical Terminology, 1997 2nd Ed Oxford: Blackwell Scientific Publications.

[26]

Balaz P, Achimovicova M, Balaz M, Billi P, Cherkezova-Zheleva Z, Criado J M, Delogu F, Dutkova E, Gaffet E, Gotor F J, Kumar R, Mitov I, Rojac T, Senna M, Streletskii A, Wieczorek-Ciurowa K. Chem. Soc. Rev., 2013, 42: 7571.

[27]

Friscic T. Chem. Soc. Rev., 2012, 41: 3493.

[28]

James S L, Adams C J, Bolm C, Braga D, Collier P, Friscic F, Grepioni K D M, Harris G, Hyett W, Jones A, Krebs T, Mack J, Maini L, Orpen A G, Parkin I P, Shearouse W C, Steed J W, Waddell D C. Chem. Soc. Rev., 2012, 41: 413.

[29]

Friscic T, Reid D G, Halasz I, Stein R S, Dinnebier R E, Duer M J. Angew. Chem. Int. Ed., 2010, 49: 712.

[30]

Bernhardt F, Trotzki R, Szuppa T, Stolle A, Ondruschka B. Beilstein, J. Org. Chem., 2010, 6: 7.

[31]

Galvez J, Galvez-Llompart M, Garcia D R. Green Chem., 2010, 12: 1056.

[32]

Cravotto G, Garella D, Tagliapietra S, Stolle A, Schußler S, Leonhardt S E S, Ondruschka B. New J. Chem., 2012, 36: 1304.

[33]

Thorwirth R, Stolle A, Ondruschka B. Green Chem., 2010, 12: 985.

[34]

Fulmer D A, Shearouse W C, Medonza S T, Mack J. Green Chem., 2009, 11: 1821.

[35]

Luque R, MacQuarie D. J. Org. Biomol. Chem., 2009, 7: 1627.

[36]

Jia C, Chen D, Zhang C, Zhang Q, Cao B, Zhao Z. Tetrahedron, 2013, 69: 7320.

[37]

Jorres M, Mersmann S, Raabe G, Bolm C. Green Chem., 2013, 15: 612.

[38]

Choudhary G, Peddinti R K. Green Chem., 2011, 13: 276.

[39]

Waddell D C, Clark T D, Mack J. Tetrahedron Lett., 2012, 53: 4510.

[40]

Hernandez J G, Juaristi E. Tetrahedron, 2011, 67: 6953.

[41]

Hernandez J G, Juaristi E. J. Org. Chem., 2011, 76: 1464.

[42]

Banon-Caballero A, Guillena G, Najera C. Green Chem., 2010, 12: 1599.

[43]

Watanabe H, Senna M. Tetrahedron Lett., 2005, 46: 6815.

[44]

Zhang Z, Peng Z W, Hao M F, Gao J G. Synlett, 2010, 2895.

[45]

Thorwirth R, Stolle A, Ondruschka B, Wild A, Schubert U S. Chem. Commun., 2011, 47: 4370.

[46]

Wada S, Suzuki H. Tetrahedron Lett., 2003, 44: 399.

[47]

Mohanram I, Meshram J, Shaikh A, Kandpal B. Synthetic Communications, 2013, 43: 3322.

[48]

Schmidt R, Thorwirth R, Szuppa T, Stolle A, Ondruschka B, Hopf H. Chem. Eur. J., 2011, 17: 8129.

[49]

Cook T L, Walker J A Jr., Mack J. Green Chem., 2013, 15: 617.

AI Summary AI Mindmap
PDF

143

Accesses

0

Citation

Detail

Sections
Recommended

AI思维导图

/