Oxidative Cyclization of Aromatic Aldehyde N‐Acylhydrazones by bis(Trifluoroacetoxy)iodobenzene

References

• Omar , F. A. , Mahfouz , N. M. and Rahman , M. A. 1996 . Design, synthesis and antiinflammatory activity of some 1,3,4‐oxadiazole derivatives . Eur. J. Med. Chem. , 31 : 819 – 825 .
   PubMed Web of Science ®Google Scholar
• Goswami , B. N. , Kataky , J. C. S. , Baruah , J. N. and Nath , S. C. 1984 . Synthesis of 3,5‐disubstituted 1,3,4‐oxadiazole‐2‐thiones as potential fungicidal agents . J. Heterocycl. Chem. , 21 : 205 – 208 .
   Web of Science ®Google Scholar
• Tully , W. R. , Gardner , C. R. , Gillespie , R. and Westwood , J. R. 1991 . 2‐(Thiazolyl)imidazo[1,2‐a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors . J. Med. Chem. , 34 : 2060 – 2067 .
   PubMed Web of Science ®Google Scholar
• Borg , S. , Vollinga , R. C. , Labarre , M. , Payza , K. , Terenius , L. and Luthman , K. 1999 . Design, synthesis, and evaluation of Phe‐Gly mimetics: Heterocyclic building blocks for pseudopeptides . J. Med. Chem. , 42 : 4331 – 4342 .
   PubMed Web of Science ®Google Scholar
• Golfier , M. and Guillerez , M. G. 1976 . Cyclisations dipolaires I: Mecanisme de la cyclisation des dihydrazides par le reactif SOCl2/pyridine . Tetrahedron Lett. , 17 : 267 – 270 .
   Google Scholar
• John , P. I. , Kathleen , S. G. , John , T. G. and Glenn , N. C. 1988 . Synthesis and insecticidal activity of some 2,5‐(fluoroalkoxyphenyl)‐1,3,4‐oxadiazoles and their N,N′‐dibenzoylhydrazine precursors . J. Chem. Eng. Data , 33 : 385 – 387 .
   Web of Science ®Google Scholar
• Carlsen , P. H. J. and Jorgensen , K. B. 1994 . Synthesis of unsymmetrically substituted 4H‐1,2,4‐triazoles . J. Heterocycl. Chem. , 31 : 805 – 807 .
   Web of Science ®Google Scholar
• Brown , P. , Best , D. J. , Broom , N. J. P. , Cassels , R. , O'Hanlon , P. J. , Mitchell , T. J. , Osborne , N. F. and Wilson , J. M. 1997 . The chemistry of pseudomonic acid, 18 heterocyclic replacement of the α,β‐unsaturated ester: Synthesis, molecular modeling, and antibacterial activity . J. Med. Chem. , 40 : 2563 – 2570 .
   PubMed Web of Science ®Google Scholar
• Liras , S. , Allen , M. P. and Segelstein , B. E. 2000 . A mild method for the preparation of 1,3,4‐oxadiazoles: Triflic anhydride promoted cyclization of diacylhydrazines . Synth. Commun. , 30 : 437 – 443 .
   Web of Science ®Google Scholar
• Löffler , J. and Schobert , R. 1997 . Synthesis of 1,3,4‐oxadiazoles from carboxylic hydrazides and of 1,2‐oxazin‐6‐ones from α‐(hydroxyimino)carboxylic esters with keteneylidene triphenylphosphorane . Synlett , : 283 – 284 .
   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
• Park , Y.‐D. , Kim , J.‐J. , Chung , H.‐A. , Kweon , 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
• Milcent , R. and Barbier , G. 1983 . Oxydation d'hydrazones par le bioxyde de plomb: Nouvelles syntheses d'oxadiazoles‐1,3,4 et de derives de l'amino‐4 triazol‐1,2,4 one‐5 . J. Heterocycl. Chem. , 20 : 77 – 80 .
   Web of Science ®Google Scholar
• Reddy , P. S. N. and Reddy , P. P. 1987 . Fusion of aroylhydrazines with acids—a new synthesis of 2,5‐diaryl‐1,3,4‐oxadiazoles . Indian J. Chem. , 26B : 890 – 891 .
   Google Scholar
• Chiba , T. and Okimoto , M. 1992 . Eletrooxidative cyclization of N‐acylhydraoznes of aldehydes and ketones to Δ3‐1,3,4‐oxadiazoles and 1,3,4‐oxadiazoles . J. Org. Chem. , 57 : 1375 – 1379 .
   Web of Science ®Google Scholar
• Yang , R.‐Y. and Dai , L.‐X. 1993 . Hypervalent iodine oxidation of N‐acylhydraoznes and N‐phenylsemicarbozone: An efficient method for the synthesis of derivertives of 1,3,4‐oxadiazoles and Δ3‐1,3,4‐oxadiazolines . J. Org. Chem. , 58 : 3381 – 3383 .
   Web of Science ®Google Scholar
• Prakash , O. , Sharma , V. , Batra , H. , Rani , N. , Sharma , P. K. and Singh , S. P. 1998 . Hypervalent iodine mediated synthesis of the heterochyclyly‐1,3,4‐oxadiazoles . Indian J. Chem. , 37B : 797 – 800 .
   Google Scholar
• Jedlovská , E. and Leško , J. 1994 . A simple one‐pot procedure for the synthesis of 1,3,4‐oxadiazoles . Synth. Commun. , 24 : 1879 – 1885 .
   Web of Science ®Google Scholar
• Gillis , B. T. and Lamontagne , M. P. 1967 . The oxidation of azines with lead tetra‐acetate . J. Org. Chem. , 32 : 3318 – 3320 .
   Web of Science ®Google Scholar
• Shang , Z.‐H. , Reiner , J. , Chang , J.‐B. and Zhao , K. 2005 . Oxidative cyclization of aldazines with bis(trifluoroacetoxy)iodobenzene . Tetrahedron Lett. , 46 : 2701 – 2704 .
   Web of Science ®Google Scholar
• Zhdankin , V. V. and Stang , J. P. 2002 . Recent developments in the chemistry of polyvalent iodine compounds . Chem. Rev. , 102 : 2523 – 2584 .
   PubMed Web of Science ®Google Scholar
• Stang , J. P. 1996 . Organic polyvalent iodine compounds . Chem. Rev. , 96 : 1123 – 1178 .
   PubMed Web of Science ®Google Scholar
• Varvoglis , A. 1984 . Polyvalent iodine compounds in organic synthesis . Synthesis , : 709 – 726 .
   Google Scholar
• Moriarity , R. M. and Prakash , O. 1998 . Synthesis of heterocyclic compounds using organohypervalent iodine reagents . Adv. Heterocycl. Chem. , 69 : 1 – 79 .
   Web of Science ®Google Scholar
• Koser , G. F. 2004 . The synthesis of heterocyclic compounds with hypervalent organoiodine reagents . Adv. Heterocycl. Chem. , 86 : 225 – 292 .
   Web of Science ®Google Scholar
• Scott , F. L. and Butler , R. N. 1966 . The reactions of lead tetra‐acetate with substituted hydrazones . J. Chem. Soc. , : 1202 – 1206 .
   Google Scholar
• Dahie , N. and Doyle , W. Combating unwanted vegetation with 2‐aryl‐5‐substituted 1,3,4‐oxadiazoles . US Patent 3808223 . 1974 .
   Google Scholar
• Huisgen , R. D. 1960 . Bildung von 1,3,4‐oxdiazolen bei der acylierang 5‐substituierter tetrazole . Chem. Ber. , 93 : 2106 – 2124 .
   Google Scholar
• Hou , S.‐J. and Chan , W.‐K. 2002 . Preparation of functionalized polystyrene‐block‐polyisoprene copolymers and their luminescence properties . Macromolecules , 35 : 850 – 856 .
   Web of Science ®Google Scholar
• Huang , X. and Zhu , Q. 2000 . The application of cross‐linked poly[styrene(iodosodiacetate)] to the synthesis of 1,3,4‐oxadiazoles . J. Chem. Res., Synop. , : 300 – 301 .
   Web of Science ®Google Scholar
• Bentiss , F. and Largrenée , M. 1999 . A new synthesis of symmetrical 2,5‐disubstituted 1,3,4‐oxadiazoles . J. Heterocycl. Chem. , 36 : 1029 – 1032 .
   Web of Science ®Google Scholar
• Jediovska , E. and Gavlakova , E. 1994 . Synthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles and their precusors . Collect. Czech, Chem. , 59 : 1892 – 1896 .
   Google Scholar
• Sain , B. and Sandhu , J. S. 1992 . N,N‐Dimethylchlorosulfite methaniminium chloride as a dehydrating agent—an efficient one‐pot synthesis of 1,3,4‐oxadiazoles and 4H‐3,1‐benzoxazin‐4‐ones . Indian J. Chem. , 31B : 768 – 770 .
   Google Scholar
• Dessolin , M. and Golfier , M. 1986 . An unusually fast Chapman‐like thermal rearrangement in the solid state . J. Chem. Soc., Chem. Commun. , : 38 – 39 .
   Google Scholar