One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Directly from Nitrile and Hydroxylamine Hydrochloride Under Solvent-Free Conditions Using Potassium Fluoride as Catalyst and Solid Support

REFERENCES

• Tanaka , K. Solvent-Free Organic Synthesis ; Wiley VCH : Weinheim , 2003 .
   Google Scholar
• Carroll , F. I. ; Gray , J. L. ; Abrahm , P. ; Kuzemko , M. A. ; Lewin , A. H. ; Boja , J. W. ; Kuhar , M. J. 3-Aryl-2-(3′-substituted-1′,2′,4′-oxadiazol-5′-yl) tropane analogs of cocaine: Affinities at the cocaine binding site at the dopamine, serotonin, and norepinephrine transporters . J. Med. Chem. 1993 , 36 , 2886 – 2890 .
   PubMed Web of Science ®Google Scholar
• Mathvink , R. J. ; Barritta , A. M. ; Candelore , M. R. ; Cascieri , M. A. ; Deng , L. ; Tota , L. ; Strader , C. D. ; Wyvratt , M. J. ; Fisher , M. H. ; Weber , A. E. Potent, selective human β 3 adrenergic receptor agonists containing a substituted indoline-5-sulfonamide pharmacophore. Bioorg. Med. Chem. Lett. 1999, 9, 1869–1874.
   PubMed Web of Science ®Google Scholar
• Lamattina , J. L. ; Mularski , C. J. Utility of p-nitrophenyl 3-bromo-2,2-diethoxypropionate (NPBDP) in heterocyclic synthesis . J. Org. Chem. 1984 , 49 , 4800 – 4805 .
   Google Scholar
• Liang , G. B. ; Qian , X. Oxadiazole synthesis on solid supports . Bioorg. Med. Chem. Lett. 1999 , 9 , 2101 – 2104 .
   PubMed Web of Science ®Google Scholar
• Liang , G. B. ; Feng , D. D. An improved oxadiazole synthesis using peptide coupling reagents . Tetrahedron Lett. 1996 , 37 , 6627 – 6630 .
   Web of Science ®Google Scholar
• Young , J. R. ; Devita , R. J. Novel synthesis of oxadiazoles via palladium catalysis . Tetrahedron Lett. 1998 , 39 , 3931 – 3934 .
   Web of Science ®Google Scholar
• Neidlein , R. ; Sheng , L. The syntheses of heterocyclic compounds with 1,2,4-oxadiazole as well as 1,2-pyrazole-rings . Synth. Commun. 1995 , 25 , 2379 – 2382 .
   Web of Science ®Google Scholar
• Neidlein , R. ; Sheng , L. Syntheses of 1,2,4-oxadiazole substituted pyrazole, isoxazole, and pyrimidine heterocycles . Heterocycl. Chem. 1996 , 33 , 1943 – 1947 .
   Web of Science ®Google Scholar
• (a) Clapp , L. B. 1,2,4-Oxadiazoles . Adv. Heterocycl. Chem. 1976 , 20 , 65 – 116 ; (b) Ryu , H. C. ; Hong , Y. T. ; Kang , S. K. Palladium-catalyzed carbonylative coupling of hypervalent iodonium salts with amidoximes: Synthesis of oxadiazoles . Heterocycles. 2001 , 54 , 985 – 988 ; (c) Bell , C. L. ; Nambury , C. N. V. ; Bauer , L. The structure of amidoximes . J. Org. Chem. 1964 , 29 , 2873 – 2877 ; (d) Eloy , F. ; Lenaers , R. The chemistry of amidoximes and related compounds . Chem. Rev. 1962 , 62 , 155 – 183 ; (e) Kayukova1 , L. A. Drug synthesis methods and manufacturing technology synthesis of 1,2,4-oxadiazoles (a review) . Pharm. Chem. J. 2005 , 39 , 539 – 547 .
   Web of Science ®Google Scholar
• Anastas , P. T. ; Kirchhoff , M. M. Origins, current status, and future challenges of green chemistry . Acc. Chem. Res. 2002 , 35 , 686 – 694 .
   PubMed Web of Science ®Google Scholar
• (a) Adib , M. ; Mahdavi , M. ; Mahmoodi , N. ; Pirelahi , H. ; Bijanzadeh , H. R. A novel, one-pot, three-component synthesis of 1,2,4-oxadiazoles under microwave irradiation and solvent-free conditions . Synlett. 2006 , 1765 – 1767 ; (b) Khan , K. M. ; Shahzad , S. A. ; Rani , M. ; Ali , M. ; Perveen , S. ; Anwar , A. ; Voelter , W. Synthesis of 5-substituted-1,3,4-oxadiazole-2(3H)-thiones under microwave irradiation . Lett. Org. Chem. 2006 , 3 , 286 – 288 ; (c) Adib , M. ; Jahromi , A. H. ; Tavoosi , N. ; Mahdavi , M. ; Bijanzadeh , H. R. Microwave-assisted efficient, one-pot, three-component synthesis of 3,5-disubstituted 1,2,4-oxadiazoles under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 2965 – 2967 ; (d) Wang , Y. ; Miller , R. L. ; Sauer , D. R. ; Djuric , S. W. Rapid and efficient synthesis of 1,2,4-oxadiazoles utilizing polymer-supported reagents under microwave heating . Org. Lett. 2005 , 7 , 925 – 928 ; (d) Santagada , V. ; Frecentese , F. ; Perissutti , E. ; Cirillo , D. ; Terracciano , S. ; Caliendo , G. A suitable 1,2,4-oxadiazoles synthesis by microwave irradiation . Bioorg. Med. Chem. Lett. 2004 , 14 , 4491 – 4493 ; (e) Evans , M. D. ; Ring , J. ; Schoen , A. ; Bell , A. ; Edwards , P. ; Berthelot , D. ; Nicewonger , R. ; Baldino , C. M. The accelerated development of an optimized synthesis of 1,2,4-oxadiazoles: Application of microwave irradiation and statistical design of experiments . Tetrahedron Lett. 2003 , 44 , 9337 – 9341 .
   Google Scholar
• Outirite , M. ; Lebrini , M. ; Legenee , M. ; Bentiss , F. New one-step synthesis of 3,5-disubstituted 1,2,4-oxadiazoles . J. Heterocycl. Chem. 2007 , 44 , 1529 – 1531 .
   Google Scholar
• Kaboudin , B. ; Saadati , F. Magnesia-supported hydroxylamine hydrochloride in the presence of sodium carbonate as an efficient reagent for the synthesis of 1,2,4-oxadiazoles from nitriles . Tetrahedron Lett. 2007 , 48 , 2829 – 2832 .
   Web of Science ®Google Scholar
• (a) Gangloff , A. R. ; Litvak , J. ; Shelton , J. E. J. ; Sperandio , D. ; Wang , V. R. ; Rice , K. D. Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst. Tetrahedron Lett. 2001, 42, 1441–1443; (b) Hebert , N. ; Hannah , A. L. ; Sutton , S. C. Synthesis of oxadiazoles on solid support. Tetrahedron Lett. 1999, 40, 8547–8550.
   Web of Science ®Google Scholar
• Rand , L. ; Wagner , W. ; Warner , P. O. ; Kovac , L. R. Reactions catalyzed by potassium fluoride, II: The conversion of adipic acid to cyclopentanone . J. Org. Chem. 1962 , 27 , 1034 – 1035 .
   Google Scholar
• Le Goff , E. The synthesis of hexaphenylpentalene . J. Am. Chem. Soc. 1962 , 84 , 3975 – 3976 .
   Google Scholar
• Rand , L. ; Swisher , J. V. ; Cronin , C. Reactions catalyzed by potassium fluoride, III: The Knoevenagel reaction . J. Org. Chem. 1962 , 27 , 3505 – 3507 .
   Web of Science ®Google Scholar
• Paquette , L. A. In Encyclopedia of Reagents for Organic Synthesis ; John Wiley & Sons : Chichester , 1995 ; vol. 4 , pp. 2760 – 2764 .
   Google Scholar
• (a) Nicolaides , N. D. ; Litinas , E. K. ; Vrasidas , I. ; Fylaktakidou , C. K. Thermal transformation of arylamidoximes in the presence of phosphorous ylides: Unexpected formation of 3-aryl-5-arylamino 1,2,4-oxadiazole . J. Heterocycl. Chem. 2004 , 41 , 499 – 503 ; (b) Leite , L. ; Srivastava , R. ; Cavalcanti , A. Thermal reactions of arylamidoximes . Bulletin des Societes Chimiques Belge. 1989 , 96 , 203 – 210 ; (c) Etsuko , K. ; Katsumi , T. Reaction of benzamideoxime with DCC . J. Heterocycl. Chem. 1986 , 23 , 1657 – 1660 .
   Google Scholar
• Eloy , F. A review of the chemistry of 1,2,4-oxadiazoles . Fortschr. Chem. Forsch. 1965 , 4 , 807 – 876 .
   Google Scholar
• Kaboudin , B. ; Navaee , K. One-pot synthesis of 1,2,4-oxadiazoles mediated by microwave irradiation under solvent-free condition . Heterocycles 2003 , 60 , 2287 – 2289 .
   Web of Science ®Google Scholar