An Improved Synthesis of 2-Aryl- and 2-Alkenyl-1,3,4-oxadiazoles by Using Copper(II) Oxide Nanoparticles as a Catalyst

N. Salva Reddy; P. Raghavendar Reddy; Biswanath Das

doi:10.1055/s-0034-1380923

Synthesis, Table of Contents

Synthesis 2015; 47(18): 2831-2838
DOI: 10.1055/s-0034-1380923

paper

An Improved Synthesis of 2-Aryl- and 2-Alkenyl-1,3,4-oxadiazoles by Using Copper(II) Oxide Nanoparticles as a Catalyst^[1]

N. Salva Reddy

Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Email: biswanathdas@yahoo.com

,

P. Raghavendar Reddy

Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Email: biswanathdas@yahoo.com

,

Biswanath Das*

Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Email: biswanathdas@yahoo.com

› Author Affiliations

Abstract

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Abstract

2-Aryl- and 2-alkenyl-1,3,4-oxadiazoles were efficiently synthesized in high yields by treatment of 1,3,4-oxadiazoles with aryl or alkenyl halides, respectively, in the presence of copper(II) oxide nanoparticles as a catalyst. The reusability of the catalyst is an important advantage in relation to practical applications of this synthesis.

Key words

oxadiazoles - copper - catalysis - nanoparticles - arylations - alkenylations

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References

References
1 Part 237 in the series Studies on Novel Synthetic Methodologies.
2 Leung D, Du W, Hardouin C, Cheng H, Hwang I, Cravatt BF, Boger DL. Bioorg. Med. Chem. Lett. 2005; 15: 1423

3a Rostom SA. F, Shalaby MA, El-Demellawy MA. Eur. J. Med. Chem. 2003; 38: 959
3b Jha KK, Samad A, Kumar Y, Shaharyar M, Khosa RL, Jain J, Kumar V, Sing P. Eur. J. Med. Chem. 2010; 45: 4963
3c Singh P, Jangra PK. Der Chem. Sin. 2010; 1 () 118

4 Singh S, Sharma LK, Saraswat A, Siddiqui IR, Kheri HK, Singh RK. P. RSC Adv. 2013; 3: 4237

5a Mitschke U, Bäuerle P. J. Mater. Chem. 2000; 10: 1471
5b Zarudnitskii EV, Pervak II, Merkulov AS, Yurchenko AA, Tolmachev AA. Tetrahedron 2008; 64: 10431

6a Yang X, Müller DC, Neher D, Meerholz K. Adv. Mater. (Weinheim, Ger.) 2006; 18: 948
6b He GS, Tan L.-S, Zhang Q, Prasad PN. Chem. Rev. 2008; 108: 1245

7a Das B, Reddy GC, Balasubramanyam P, Salvanna N. Tetrahedron 2012; 68: 300
7b Salvanna N, Reddy GC, Rao BR, Das B. RSC Adv. 2013; 3: 20538
7c Salvanna N, Reddy GC, Das B. Tetrahedron 2013; 69: 2220
7d Salvanna N, Das B. Synlett 2014; 25: 2033

For some recent examples, see:

8a Yanagisawa S, Sudo T, Noyori R, Itami K. J. Am. Chem. Soc. 2006; 128: 11748
8b Stuart DR, Villemure E, Fagnou K. J. Am. Chem. Soc. 2007; 129: 12072
8c Zhao J, Zhang Y, Cheng K. J. Org. Chem. 2008; 73: 7428
8d Yang S.-D, Sun C.-L, Fang Z, Li B.-J, Li Y.-Z, Shi Z.-J. Angew. Chem. Int. Ed. 2008; 47: 1473
8e Besselièvre F, Piguel S, Mahuteau-Betzer F, Grierson DS. Org. Lett. 2008; 10: 4029
8f Monnier F, Turtaut F, Duroure L, Taillefer M. Org. Lett. 2008; 10: 3203
8g Mukai T, Hirano K, Satoh T, Miura M. J. Org. Chem. 2009; 74: 6410
8h Ackermann L, Althammer A, Fenner S. Angew. Chem. Int. Ed. 2009; 48: 201
8i Join B, Yamamoto T, Itami K. Angew. Chem. Int. Ed. 2009; 48: 3644
8j Kobayashi O, Uraguchi D, Yamakawa T. Org. Lett. 2009; 11: 2679
8k Verrier C, Hoarau C, Marsais F. Org. Biomol. Chem. 2009; 7: 647
8l Miyasaka M, Hirano K, Satoh T, Miura M. J. Org. Chem. 2010; 75: 5421
8m Liao Q, Zhang L, Li S, Xi C. Org. Lett. 2011; 13: 228

9a Hilf C, Bosold F, Harms K, Marsch M, Boche G. Chem. Ber. 1997; 130: 1213
9b Sánchez RS, Zhuravlev FA. J. Am. Chem. Soc. 2007; 129: 5824
9c Rout L, Sen TK, Punniyamurthy T. Angew. Chem. Int. Ed. 2007; 46: 5583
9d Shen K, Fu Y, Li J.-N, Liu L, Guo Q.-X. Tetrahedron 2007; 63: 1568
9e Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2008; 130: 1128
9f Brasche G, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 1932
9g Jammi S, Sakthivel S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T. J. Org. Chem. 2009; 74: 1971
9h Pirrung MC, Ghorai S, Ibarra-Rivera TR. J. Org. Chem. 2009; 74: 4110
9i Kawano T, Yashizumi T, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 3072
9j Monguchi D, Yamamura A, Fujiwara T, Somete T, Mori A. Tetrahedron Lett. 2010; 51: 850
9k Polshettiwar V, Varma RS. Green Chem. 2010; 12: 743
9l Xu J, Luo D.-F, Xiao B, Liu Z.-J, Gong T.-J, Fu Y, Liu L. Chem. Commun. 2011; 47: 4300
9m Tomashenko OA, Escudero-Adán EC, Martínez Belmonte M, Grushin VV. Angew. Chem. Int. Ed. 2011; 50: 7655
9n Zhao X, Wu G, Zang Y, Wang J. J. Am. Chem. Soc. 2011; 133: 3296

10a Zhang W, Zeng Q, Zhang X, Tian Y, Yue Y, Guo Y, Wang Z. J. Org. Chem. 2011; 76: 4741
10b Zhang W, Tian Y, Zhao N, Wang Y, Li J, Wang Z. Tetrahedron 2014; 70: 6120
10c Murty MS. R, Penthala R, Buddana SK, Prakasham RS, Das P, Polepalli S, Jain N, Bojja S. Med. Chem. Res. 2014; 23: 4579

11a Durán Pachón L, van Maarseveen JH, Rothenberg G. Adv. Synth. Catal. 2005; 347: 811
11b Zhang W, Qi H, Li L, Wang X, Chen J, Peng K, Wang Z. Green Chem. 2009; 11: 1194
11c Sreedhar B, Arundhathi R, Reddy PL, Kantam ML. J. Org. Chem. 2009; 74: 7951
11d Reddy VP, Kumar AV, Swapna K, Rao KR. Org. Lett. 2009; 11: 1697
11e Polshettiwar V, Varma RS. Green Chem. 2010; 12: 743

12 Ranu BC, Dey R, Chatterjee T, Ahammed S. ChemSusChem 2012; 5: 22

An Improved Synthesis of 2-Aryl- and 2-Alkenyl-1,3,4-oxadiazoles by Using Copper(II) Oxide Nanoparticles as a Catalyst[1]

An Improved Synthesis of 2-Aryl- and 2-Alkenyl-1,3,4-oxadiazoles by Using Copper(II) Oxide Nanoparticles as a Catalyst^[1]