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Synlett 2014; 25(14): 2033-2035
DOI: 10.1055/s-0034-1378361
DOI: 10.1055/s-0034-1378361
letter
Synthesis of 2-Alkynyl 1,3,4-Oxadiazoles by Palladium-Catalyzed Cross- Coupling Reaction[1]
Further Information
Publication History
Received: 15 April 2014
Accepted after revision: 30 May 2014
Publication Date:
16 July 2014 (online)
Abstract
Several 2-alkynyl 1,3,4-oxadiazoles have been synthesized efficiently by employing palladium-catalyzed cross-coupling under Sonogashira reaction conditions. This reaction has been applied for the first time for the preparation of oxadiazole derivatives. The products were formed in high yields and no side products were detected.
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References and Notes
- 1 Part 236 in the series ‘Studies on novel synthetic methodologies’.
- 2a Rostom SA. F, Shalaby MA, El-Demellawy MA. Eur. J. Med. Chem. 2003; 38: 959
- 2b Jha KK, Samad A, Kumar Y, Shaharyar M, Khosa RL, Jain J, Kumar V, Sing P. Eur. J. Med. Chem. 2010; 45: 4963
- 2c Singh P, Jangra PK. Der Chemica Sinica 2010; 1: 118
- 3 Leung D, Du W, Hardouin C, Cheng H, Hwang I, Cravatt BF, Boger DL. Bioorg. Med. Chem. Lett. 2005; 15: 1423
- 4a He GS, Tan L-S, Zheng Q, Prasad PN. Chem. Rev. 2008; 108: 1245
- 4b Guin S, Ghosh T, Rout SK, Banarjee A, Patel BK. Org. Lett. 2011; 13: 5976
- 5 Singh S, Sharma LK, Saraswat A, Siddiqui IR, Kheri HK, Singh RK. P. RSC Adv. 2013; 3: 4237
- 6a Mitschke U, Bauerle P. J. Mater. Chem. 2000; 10: 1471
- 6b Zarudnitskii EV, Pervak II, Merkulov AS, Yurchenko AA, Tolmachev AA. Tetrahedron 2008; 64: 10431
- 7a Thorand S, Krause N. J. Org. Chem. 1998; 63: 8551
- 7b Hundertmark T, Litter AF, Buchwald SL, Fu GC. Org. Lett. 2000; 2: 1729
- 7c Chow H.-F, Wan C.-W, Low K.-H, Yeung Y.-Y. J. Org. Chem. 2001; 66: 1910
- 7d Sonogashira K. J. Organomet. Chem. 2002; 653: 46
- 7e Eberhard MR, Wang Z, Jensen CM. Chem. Commun. 2002; 818
- 7f Choudary BM, Madhi S, Chowdari NS, Kantam ML, Sreedhar B. J. Am. Chem. Soc. 2002; 124: 14127
- 7g Kollhofer A, Pullmann T, Plenio H. Angew. Chem. 2003; 115: 1086
- 7h Hierso J.-C, Fihri A, Amardeil R, Meunier P. Org. Lett. 2004; 6: 3473
- 7i Son SU, Jang Y, Park J, Na HB, Park HM, Yun HJ, Lee J, Hyeon T. J. Am. Chem. Soc. 2004; 126: 5026
- 7j Feuerstein M, Doucet H, Santelli M. Tetrahedron Lett. 2004; 45: 8443
- 8a Tykwinski RR. Angew. Chem. Int. Ed. 2003; 42: 1566
- 8b Lu L, Yan H, Sun P, Zhu Y, Yang H, Liu D, Rong G, Mao J. Eur. J. Org. Chem. 2013; 1644
- 9a Reddy GC, Balasubramanyam P, Salvanna N, Das B. Eur. J. Org. Chem. 2012; 471
- 9b Das B, Reddy GC, Balasubramanyam P, Salvanna N. Tetrahedron 2012; 68: 300
- 9c Salvanna N, Reddy GC, Das B. Tetrahedron 2013; 69: 2220
- 9d Salvanna N, Reddy GC, Rao BR, Das B. RSC Adv. 2013; 3: 20538
- 10 Boga C, Del Vecchio E, Forlani L, Todesco PE. J. Organomet. Chem. 2000; 601: 233
- 11a Gelman D, Buchwald SL. Angew. Chem. Int. Ed. 2003; 42: 5993
- 11b Doucet H, Hierso JC. Angew. Chem. Int. Ed. 2007; 46: 834
- 11c Wolff O, Waldvogel SR. Synthesis 2007; 761
- 11d Chinchilla R, Najera C. Chem. Rev. 2007; 107: 874
- 11e Ullah F, Dang TT, Heinicke J, Villiger A, Langer P. Synlett 2009; 838
- 11f Manarin F, Roehrs JA, Branda O, Nogueira CW, Zeni G. Synthesis 2009; 4001
- 11g Sajith AM, Muralidharan A. Tetrahedron Lett. 2012; 53: 5206