Silica Sulfuric Acid: An Efficient and Versatile Acidic Catalyst for the Rapid and Ecofriendly Synthesis of 1,3,4‐Oxadiazoles at Ambient Temperature

References

• Kolb , H. C. , Finn , M. G. and Sharpless , K. B. 2001 . Click chemistry: Diverse chemical function from a few good reactions . Angew. Chem. Int. Ed. , 40 : 2004 – 2021 .
   PubMed Web of Science ®Google Scholar
• Kolb , H. C. and Sharpless , K. B. 2003 . The growing impact of click chemistry on drug discovery . Drug Discovery Today , 8 : 1128 – 1137 .
   PubMed Web of Science ®Google Scholar
• Shi , W. , Qian , X. , Zhang , R. and Song , G. 2001 . Synthesis and quantitative structure–activity relationships of new 2,5‐disubstituted‐1,3,4‐oxadiazoles . J. Agric. Food Chem. , 49 : 124 – 130 .
   PubMed Web of Science ®Google Scholar
• Meng , H. and Hung , W. 2000 . Novel photoluminescent polymers containing oligothiophene and m‐phenylene‐1,3,4‐oxadiazole moieties: Synthesis and spectroscopic and electrochemical studies . J. Org. Chem. , 65 : 3894 – 3901 .
   PubMed Web of Science ®Google Scholar
• Meng , H. , Chen , Z. , Liu , X. , Lia , Y. , Chua , S. and Huang , W. 1999 . Synthesis and characterization of a novel blue electroluminescent polymer constituted of alternating carbazole and aromatic oxadiazole units . Phys. Chem. Chem. Phys. , 1 : 3123 – 3127 .
   Google Scholar
• Bottino , F. A. , Pasquale , G. D. and Innelli , P. 2001 . Synthesis, characterization, and study of the thermal properties of new poly(arylene ether 1,3,4‐oxadiazoles) . Macromolecules , 34 : 33 – 37 .
   Web of Science ®Google Scholar
• Tamoto , N. , Adachi , C. and Nagai , K. 1997 . Electroluminescence of 1,3,4‐oxadiazole and triphenylamine‐containing molecules as an emitter in organic multilayer light emitting diodes . Chem. Mater. , 9 : 1077 – 1085 .
   Web of Science ®Google Scholar
• Perez , M. A. and Bermejo , J. M. 1993 . Synthesis of multidentate 1,3,4‐oxadiazole containing, imine‐containing, and phenol‐containing macrocycles . J. Org. Chem. , 58 : 2628 – 2630 .
   Web of Science ®Google Scholar
• Lee , D. W. , Kwon , K.‐Y. , Jin , J. I. , Park , Y. , Kim , Y.‐R. and Hwang , I.‐W. 2001 . Luminescence properties of structurally modified PPVs: PPV derivatives bearing 2‐(4‐tert‐butylphenyl)‐5‐phenyl‐1,3,4‐oxadiazole pendants . Chem. Mater. , 13 : 565 – 574 .
   Google Scholar
• Orlek , B. S. , Blaney , F. E. , Brown , F. , Clark , M. S. G. , Hadley , M. S. , Hatcher , J. , Riley , G. J. , Rosenberg , H. E. , Wadsworth , H. J. and Wyman , P. 1991 . Comparison of azabycyclic esters and oxadiazoles as ligands for the muscarinic receptor . J. Med. Chem. , 34 : 2726 – 2735 .
   PubMed Web of Science ®Google Scholar
• Watjen , F. , Baker , R. , Engelstoff , M. , Herbert , R. , MacLeod , A. , Knight , A. , Merchant , K. , Moseley , J. , Saunders , J. , Swain , C. J. , Wong , E. and Springer , J. P. 1989 . Novel benzodiazepine receptor partial agonists—Oxadiazolylimidazobenzodiazepines . J. Med. Chem. , 32 : 2282 – 2291 .
   PubMed Web of Science ®Google Scholar
• Carroll , F. I. , Gray , J. L. , Abrahm , P. , Kuzemko , M. A. , Lewin , A. H. , Boja , J. W. and Kuhar , M. J. 1993 . 3‐Aryl‐2‐(3′‐substituted‐1′,2′,4′‐oxadiazol‐5′‐yl)tropain analogs of cocaine—Affinities at the cocaine binding‐site at the dopamine, serotonin, and norepinephrine transporters . J. Med. Chem. , 36 : 2886 – 2890 .
   PubMed Web of Science ®Google Scholar
• Diana , G. D. , Volkots , D. L. , Nitz , T. J. , Bailey , T. R. , Long , M. A. , Vescio , N. , Aldous , S. , Pevear , D. C. and Dutko , F. J. 1994 . Oxadiazoles as ester bioisosteric replacementes in compounds related to disoxaril—antirhinovirus activity . J. Med. Chem. , 37 : 2421 – 2436 .
   PubMed Web of Science ®Google Scholar
• Ankersen , M. , Peschke , B. , Hansen , B. S. and Hansen , T. K. 1997 . Investigation of bioisosters of the growth hormone secretagogue L‐692,429 . Bioorg. Med. Chem. Lett. , 7 : 1293 – 1298 .
   Web of Science ®Google Scholar
• Chen , H. , Li , Z. and Han , Y. 2000 . J. Agric. Food Chem. , 48 : 5312 – 5315 .
   PubMed Web of Science ®Google Scholar
• Deshmukh , A. A. , Sattur , P. B. and Sheth , U. K. 1976 . Synthesis and pharmacology of 2,3‐diphenylpropionhydrazides and hydrazones . Indian. J. Exp. Biol. , 14 : 166 – 168 .
   PubMed Web of Science ®Google Scholar
• Sen Gupta , A. K. , Garg , M. and Chandra , U. 1979 . Synthesis and biological activity of some new N‐3(2phenyl quinazolin (3H)‐4‐one) acyl hydrazones . J. Indian Chem. Soc. , 56 : 645 – 647 .
   Google Scholar
• Zheng , X. , Li , Z. , Wang , Y. , Chen , W. , Huang , Q. , Liu , C. and Song , G. 2003 . J. Flourine Chem. , 123 : 163 – 169 .
   Web of Science ®Google Scholar
• Khan , M. T. H. , Choidhary , M. I. , Khan , K. M. , Rani , M. and Rahman , A. 2005 . Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2,5‐disubstituted‐1,3,4‐oxadiazole analogues . Bioorg. Med. Chem. , 13 : 3385 – 3395 .
   PubMed Web of Science ®Google Scholar
• Zarghi , A. , Tabatabai , S. A. , Faizi , M. , Ahadian , A. , Navabi , P. , Zanganeh , V. and Shafiee , A. 2005 . Synthesis and anticonvulsant activity of new 2‐substituted‐5‐(2‐benzyloxyphenyl)‐1,3,4‐oxadiazoles . Bioorg. Med. Chem. Lett. , 15 : 1863 – 1865 .
   PubMed Web of Science ®Google Scholar
• Hayes , F. N. , Rogers , B. S. and Ott , D. J. 1955 . 2,5‐Diaryloxazoles and 2,5‐diaryl‐1,3,4‐oxadiazoles . J. Am. Chem. Soc. , 77 : 1850 – 1852 .
   Web of Science ®Google Scholar
• El Kaim , L. , Le Menestrel , I. and Morgentin , R. 1998 . Trichloroacetic acid hydrazones I: New formation of 1,3,4‐oxadiazoles from aldehydes . Tetrahedron Lett , 39 : 6885 – 6888 .
   Web of Science ®Google Scholar
• Khan , K. M. , Ullah , Z. , Rani , M. , Perveen , S. , Haider , S. M. , Choudhary , M. I. , Rahman , A. and Voelter , W. 2004 . Microwave‐assisted synthesis of 2,5‐disubstituted‐1,3,4‐oxadiazoles . Lett. Org. Chem. , 1 : 50 – 52 .
   Web of Science ®Google Scholar
• Loffler , J. and Schobert , R. 1997 . Synthesis of 1,3,4‐oxadiazoles from carboxylic hydrazides and of 1,2‐oxazin‐6‐ones from alpha‐(hydroxyimino)carboxylic esters with keteneylidene triphenylphosphorane . Synlett , : 283 – 284 .
   Google Scholar
• Herrero , M. A. , Wannberg , J. and Larhed , M. 2004 . Direct microwave synthesis of N,N′‐diacylhydrazines and boc‐protected hydrazides by in situ carbonylations under air . Synlett , : 2335 – 2338 .
   Google Scholar
• Kosmrlj , J. , Kocevar , M. and Polanc , S. 1996 . A mild approach to 1,3,4‐oxadiazoles and fused 1,2,4‐triazoles. Diazenes as intermediates? . Synlett , : 652 – 654 .
   Google Scholar
• Rostamizadeh , S. and Housaini , G. 2004 . Microwave‐assisted syntheses of 2,5‐disubstituted 1,3,4‐oxadiazoles . Tetrahedron Lett. , 45 : 8753 – 8756 .
   Web of Science ®Google Scholar
• Rao , V. S. and Sekhar , V. G. C. 2004 . Iodobenzene diacetate mediated solid‐state synthesis of heterocyclyl‐1,3,4‐oxadiazoles . Synth. Commun. , 34 : 2153 – 2157 .
   Web of Science ®Google Scholar
• Ainsworth , C. 1955 . The condensation of aryl carboxylic acid hydrazides with orthoesters . J. Am. Chem. Soc. , 77 : 1148 – 1150 .
   Web of Science ®Google Scholar
• Leiby , R. W. J. 1984 . Heterocycl. Chem . 21 : 1825 – 1832 .
   Google Scholar
• Shafiee , A. , Naimi , E. , Mansobi , P. , Foroumadi , A. and Shekari , M. 1995 . Syntheses of substituted ‐oxazole‐1,3,4‐thiadiazoles, 1,3,4‐oxadiazoles, and 1,2,4‐triazoles . J. Heterocycl. Chem. , 32 : 1235 – 1239 .
   Web of Science ®Google Scholar
• Khajavi , M. S. , Sadat Hosseini , S. S. and Sefidkon , F. Iran . 1997 . J. Chem. Chem. Eng. , 16 : 68 – 71 .
   Google Scholar
• Brown , B. J. , Clemens , I. R. and Neesom , J. K. 2000 . Diisopropylcarbodiimide: A novel reagent for the synthesis of 1,3,4‐oxadiazoles on solid‐phase . Synlett , : 131 – 133 .
   Google Scholar
• Hebert , N. , Hannah , A. L. and Sutton , S. C. 1999 . Synthesis of oxadiazoles on solid support . Tetrahedron Lett. , 40 : 8547 – 8550 .
   Web of Science ®Google Scholar
• Brain , C. T. , Paul , J. M. , Loong , Y. and Okaley , P. J. 1999 . Novel procedure for the synthesis of 1,3,4‐oxadiazoles from 1,2‐diacylhydrazines using polymer‐supported Burgess reagent under microwave conditions . Tetrahedron Lett. , 40 : 3275 – 3278 .
   Web of Science ®Google Scholar
• Kilburn , J. P. , Lau , J. and Jones , R. C. F. 2001 . 1,3,4‐Oxadiazole formation: A novel solid support strategy . Tetrahedron Lett. , 42 : 2583 – 2586 .
   Google Scholar
• Coppo , F. T. , Evans , K. A. , Graybill , T. L. and Burton , G. 2004 . Efficient one‐pot preparation of 5‐substituted‐2‐amino‐1,3,4‐oxadiazoles using resin‐bound reagents . Tetrahedron Lett. , 45 : 3257 – 3260 .
   Web of Science ®Google Scholar
• Sugiono , E. and Detert , H. 2001 . Functionalisation of 2‐(1‐naphthyl)‐5‐phenyl‐1,3,4‐oxadiazol with alkoxysilanes . Synthesis , : 893 – 896 .
   Google Scholar
• Park , Y.‐D. , Kim , J.‐J. , Chung , H.‐A. , Keweon , D.‐H. , Cho , S.‐D. , Lee , S. G. and Yoon , Y.‐J. 2003 . Facile synthesis of symmetric and unsymmetric 1,3,4‐oxadiazoles using 2‐acyl(or aroyl)pyridazin‐3‐ones . Synthesis , : 560 – 564 .
   Web of Science ®Google Scholar
• Young , J. R. and DeVita , R. J. 1998 . Novel synthesis of oxadiazoles via palladium catalysis . Tetrahedron Lett. , 39 : 3931 – 3934 .
   Web of Science ®Google Scholar
• Dabiri , M. , Salehi , P. , Mohammadi , A. A. and Baghbanzadeh , M. 2005 . One‐pot synthesis of mono‐ and disubstituted (3H)‐quinazolin‐4‐ones in dry media under microwave irradiation . Synth. Commun. , 35 : 279 – 287 .
   Web of Science ®Google Scholar
• Salehi , P. , Dabiri , M. , Khosropour , A. R. and Roozbehniya , P. 2006 . Diammonium hydrogen phosphate: A versatile and inexpensive reagent for one‐pot synthesis of dihydropyrimidinones, quinazolinones and azalactones under solvent‐free conditions . J. Iran. Chem. Soc. , 3 : 98 – 104 .
   Web of Science ®Google Scholar
• Tanaka , K. and Toda , F. 2000 . Solvent‐free organic synthesis . Chem. Rev. , 100 : 1025 – 1047 . and other references cited therein
   PubMed Web of Science ®Google Scholar
• Zolfigol , M. A. 2001 . Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions . Tetrahedron , 57 : 9509 – 9511 .
   Web of Science ®Google Scholar
• Salehi , P. , Dabiri , M. , Zolfigol , M. A. and Baghbanzadeh , M. 2005 . A novel method for the one‐pot three‐component synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones . Synlett , : 1155 – 1157 .
   Web of Science ®Google Scholar
• Salehi , P. , Dabiri , M. , Zolfigol , M. A. and Baghbanzadeh , M. 2005 . A new approach to the facile synthesis of mono‐ and disubstituted quinazolin‐4(3H)‐ones under solvent‐free conditions . Tetrahedron Lett. , 46 : 7051 – 7053 .
   Web of Science ®Google Scholar