RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2016; 48(20): 3597-3602
DOI: 10.1055/s-0035-1562431
DOI: 10.1055/s-0035-1562431
paper
Iron(III) Chloride/l-Proline as an Efficient Catalyst for the Synthesis of 3-Substituted 1,2,4-Oxadiazoles from Amidoximes and Triethyl Orthoformate
Weitere Informationen
Publikationsverlauf
Received: 10. März 2016
Accepted after revision: 28. April 2016
Publikationsdatum:
15. Juni 2016 (online)
Abstract
A general, facile, and efficient method is presented for the synthesis of 3-substituted 1,2,4-oxadiazoles from amidoximes and triethyl orthoformate. The procedure employs an iron(III) chloride/l-proline catalytic system and the 3-substituted 1,2,4-oxadiazole products are obtained in moderate to good yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562431.
- Supporting Information
-
References
- 1a Bostrom J, Hogner A, Llinas A, Wellner E, Plowright AT. J. Med. Chem. 2012; 55: 1817
- 1b Saha R, Tanwar O, Marella A, Alam MM, Akhtar M. Mini Rev. Med. Chem. 2013; 13: 1027
- 2 Bora RO, Dar B, Pradhan V, Farooqui M. Mini Rev. Med. Chem. 2014; 14: 355
- 3 Pace A, Pierro P. Org. Biomol. Chem. 2009; 7: 4337
- 4 Xu J, Wei L, Mathvink R, He J, Park Y.-J, He H, Leiting B, Lyons KA, Marsilio F, Patel RA, Wu JK, Thornberry NA, Weber AE. Bioorg. Med. Chem. Lett. 2005; 15: 2533
- 5 Weidner-Wells MA, Henninger TC, Fraga-Spano SA, Boggs CM, Matheis M, Ritchie DM, Argentieri DC, Wachter MP, Hlasta DJ. Bioorg. Med. Chem. Lett. 2004; 14: 4307
- 6 Tyrkov AG, Sukhenko LT. Pharm. Chem. J. 2004; 38: 376
- 7 Zhang H.-Z, Kasibhatla S, Kuemmerle J, Kemnitzer W, Ollis-Mason K, Qiu L, Crogan-Grundy C, Tseng B, Drewe J, Cai SX. J. Med. Chem. 2005; 48: 5215
- 8 Lankau HJ, Unverferth K, Grunwald C, Hartenhauer H, Heinecke K, Bemoster K, Dost R, Egerland U, Rundfeldt C. Eur. J. Med. Chem. 2007; 42: 873
- 9 Huhtiniemi T, Suuronen T, Rinne VM, Wittekindt C, Lahtela-Kakkonen M, Jarho E, Wallen EA. A, Salminen A, Poso A, Leppanen J. J. Med. Chem. 2008; 51: 4377
- 10 Street LJ, Baker R, Book T, Kneen CO, MacLeod AM, Merchant KJ, Showell GA, Saunders J, Herbert RH, Freedman SB, Harley EA. J. Med. Chem. 1990; 33: 2690
- 11 Wilschanski M. Discovery Med. 2013; 15: 127
- 12a Li Z, Chen W, Hale JJ, Lynch CL, Mills SG, Hajdu R, Keohane CA, Rosenbach MJ, Milligan JA, Shei G.-J, Cherbert G, Parent SA, Bergstrom J, Card D, Forrest M, Quackenbush EJ, Wickham LA, Vargas H, Evans RM, Rosen H, Mandala S. J. Med. Chem. 2005; 48: 6169
- 12b Haugwitz RD, Martinez AJ, Venslavsky J, Angel RG, Maurer BV, Jacobs GA, Narayanan VL, Cruthers LR, Szanto J. J. Med. Chem. 1985; 28: 1234
- 13a LaMattina JL, Mularski CJ. J. Org. Chem. 1984; 49: 4800
- 13b Liang GB, Qian X. Bioorg. Med. Chem. Lett. 1999; 9: 2101
- 13c Liang GB, Feng DD. Tetrahedron Lett. 1996; 37: 6627
- 13d Young JR, DeVita RJ. Tetrahedron Lett. 1998; 39: 3931
- 14a Neidlein R, Sheng L. Synth. Commun. 1995; 25: 2379
- 14b Neidlein R, Sheng L. J. Heterocycl. Chem. 1996; 33: 1943
- 15a Clapp LB. Adv. Heterocycl. Chem. 1976; 20: 65
- 15b Ryu HC, Hong YT, Kang SK. Heterocycles 2001; 54: 985
- 15c Bell CL, Nambury CN. V, Bauer L. J. Org. Chem. 1964; 29: 2873
- 15d Eloy F, Lenaers R. Chem. Rev. 1962; 62: 155
- 16a Korbonits D, Horvath K. Heterocycles 1994; 37: 2051
- 16b Chiou S, Shine HJ. J. Heterocycl. Chem. 1989; 26: 125
- 16c Kayukova LA, Praliev KD, Zhumadildaeva IS, Klepikova SG. Chem. Heterocycl. Compd. 1999; 35: 630
- 16d Ooi NS, Wilson DA. J. Chem. Soc., Perkin Trans. 2 1980; 1792
- 16e Andersen KE, Lundt BF, Jørgensen AS, Braestrup C. Eur. J. Med. Chem. 1996; 31: 417
- 16f Kaboudin B, Saadati F. Tetrahedron Lett. 2007; 48: 2829
- 16g Kaboudin B, Saadati F. J. Heterocycl. Chem. 2005; 42: 699
- 16h Kaboudin B, Malekzadeh L. Tetrahedron Lett. 2011; 52: 6424
- 16i Kaboudin B, Navaee K. Heterocycles 2001; 55: 1443
- 17a Gangloff AR, Litvak J, Shelton JE. J, Sperandio D, Wang VR, Rice KD. Tetrahedron Lett. 2001; 42: 1441
- 17b Hebert N, Hannah AL, Sutton SC. Tetrahedron Lett. 1999; 40: 8547
- 18 Augustine JK, Akabote V, Hegde SG, Alagarsamy P. J. Org. Chem. 2009; 74: 5640
- 19 Buting WE, Cameron A. US Patent 33566984 (A), 1967
- 20 Fershtat LL, Ananyev IV, Makhova NN. RSC Adv. 2015; 5: 47248
- 21 Hemming K In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations: Five-Membered Hetarenes with Three or More Heteroatoms. Vol. 13. Storr RC, Gilchrist TL. Georg Thieme; Stuttgart: 2004: 127-184
- 22 Suresh Dhanusu S, Kuppusamy K, Kasi P. Tetrahedron Lett. 2014; 55: 3678
- 23 Steglich W, Van Ree T. Synth. Commun. 1982; 12: 457
- 24 Claisse JA, Foxton MW, Gregory GI, Sheppard AH, Tiley EP, Warburton WK, Wilson MJ. J. Chem. Soc., Perkin. Trans. 1 1973; 2241
- 25 Movassagh B, Talebsereshki F. Synth. Commun. 2014; 44: 188