Mononuclear Heterocyclic Rearrangement of 5-Arylisoxazole-3-hydroxamic Acids into 3,4-Substituted 1,2,5-Oxadiazoles

Abstract

By a series of successive transformations, 5-arylisoxazole-3-carboxylic acids (aryl = phenyl, p-tolyl, 2,5-dimethylphenyl) have been converted into 5-arylisoxazole-3-hydroxamic acids, which undergo rearrangement by the action of aqueous KOH to form 3,4-substituted 1,2,5-oxadiazoles. The structure of one of them, 1-(2,5-dimethylphenyl)-2-(4-hydroxy-1,2,5-oxadiazol-3-yl)ethanone, has been confirmed by single crystal X-ray analysis.

Key words

isoxazoles - 1,2,5-oxadiazoles - furazans - rearrangement - crystal structure - hydroxamic acids

• References

• 1a Modern Heterocyclic Chemistry . Alvarez-Builla J, Vaquero JJ, Barluenga J. Wiley-VCH; Weinheim: 2011
• 1b Cerecetto H, Porcal W. Mini-Rev. Med. Chem. 2005; 5: 57
• 1c Takabatake T, Hasewaga M, Nagano T, Hirobe M. Chem. Pharm. Bull. 1992; 40: 1644
• 2a Agrawal JP, Hodgson RD. Organic Chemistry of Explosives . Wiley; Chichester: 2007
• 2b Wang R, Guo YQ, Zeng Z, Twamley B, Shreeve JM. Chem. Eur. J. 2009; 15: 2625
• 2c Veauthier JM, Chavez DE, Tappan BC, Parrish DA. J. Energ. Mater. 2010; 28: 229
• 3 Sheremetev AB. Russ. Chem. Rev. 1999; 68: 137
• 4 Ruccia M, Vivona N, Spinelli D. Adv. Heterocycl. Chem. 1981; 29: 141
• 5a Kakkar R, Grover R, Chadha P. Org. Biomol. Chem. 2003; 1: 2200
• 5b Surova TV, Enyashin AN. J. Struct. Chem. 2003; 44: 297
• 5c Ventura ON, Rama JB, Turi L, Dannenberg GG. J. Phys. Chem. 1995; 99: 131
• 6a Potkin VI, Bumagin NA, Petkevich SK, Lyakhov AS, Rudakov DA, Livantsov MV, Golantsov NE. Synthesis 2012; 44: 151
• 6b Kulchitsky VA, Potkin VI, Zubenko YuS, Chernov AN, Talabaev MV, Demidchik YuE, Petkevich SK, Kazbanov VV, Gurinovich TA, Roeva MO, Grigoriev DG, Kletskov AV, Kalunov VN. Med. Chem. 2012; 8: 22
• 6c Potkin VI, Petkevich SK, Zalesskaya EG. Russ. J. Org. Chem. 2009; 45: 879
• 7a Li JJ. Name Reactions: A Collection of Detailed Reaction Mechanisms. Springer-Verlag; Berlin: 2003
• 7b Bauer L, Exner O. Angew. Chem., Int. Ed. Engl. 1974; 13: 376 ; Angew. Chem. 1974, 86, 419
• 7c Anilkumar R, Chandrasekhar S, Sridhar M. Tetrahedron Lett. 2000; 41: 5291
• 8 Allen FH. Acta Crystallogr., Sect B 2002; 58: 380
• 9 CCDC 903835 contains the supplementary crystallographic data for 18. These data can be obtained via http://www.ccdc.cam.ac.uk/conts/retrieving.html, free of charge or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; e-mail: [e-mail] or fax: [phone].
• 10 Burla MC, Caliandro R, Camalli M, Carrozzini B, Cascarano GL, De Caro L, Giacovazzo C, Polidori G, Spagna R. J. Appl. Crystallogr. 2005; 38: 381
• 11 Sheldrick GM. Acta Crystallogr., Sect A 2008; 64: 112
• 12 Spek AL. Acta Crystallogr., Sect. D. 2009; 65: 148