Silica-Supported Ferric Chloride (FeCl₃-SiO₂): An Efficient and Recyclable Heterogeneous Catalyst for the Preparation of Arylaminotetrazoles

REFERENCES

• Bulter , R. N. In Comprehensive Heterocyclic Chemistry II ; A. R. Katritzky , C. W. Ress , E. F. V. Scriven (Eds.); Pergamon : New York , 1996 ; vol. 4 , p. 621 .
   Google Scholar
• (a) Herr , R. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: Medicinal chemistry and synthetic methods . J. Bioorg. Med. Chem. 2002 , 10 , 3379 ; (b) Holland , G. F. ; Pereira , J. N. Heterocyclic tetrazoles, a new class of lipolysis inhibitors . J. Med. Chem. 1967 , 10 , 149 ; (c) Figdor , S. K. ; Schach von Wittenau , M. Metabolism of 5-(3-pyridyl)tetrazole . J. Med. Chem. 1967 , 10 , 1158 ; (d) Rhonnstad , P. ; Wensbo , D. On the relative strength of the 1H-tetrazol-5-yl- and the 2-(triphenylmethyl)-2H-tetrazol-5-yl-group in directed ortho-lithiation . Tetrahedron Lett. 2002 , 43 , 3137 .
   PubMed Web of Science ®Google Scholar
• Klapötke , T. M. ; Stierstorfer , J. ; Weber , B. New energetic material: Synthesis and characterization of copper 5-nitriminotetrazolates . Inorg. Chim. Acta 2009 , 362 , 2311 .
   Web of Science ®Google Scholar
• John , E. O. ; Kirchmeier , R. L. ; Shreeve , J. M. Reactions of 5-(perfluoro-alkyl)tetrazolates with cyanogen, nitrosyl, and cyanuric chlorides . Inorg. Chem. 1989 , 28 , 4629 .
   Web of Science ®Google Scholar
• Modarresi-Alam , A. R. ; Khamooshi , F. ; Rostamizadeh , M. ; Keykha , H. ; Nasrollahzadeh , M. ; Bijanzadeh , H. R. ; Kleinpeter , E. Dynamic 1H NMR spectroscopic study of the restricted S-N rotation in aryl-N-(arylsulfonyl)-N-(triphenylphosphoranylidene)imidocarbamates . J. Mol. Struc. 2007 , 841 , 67 .
   Web of Science ®Google Scholar
• Finnegan , W. G. ; Henry , R. A. ; Lieber , E. Preparation and isomerization of 5-alkylaminotetrazoles . J. Org. Chem. 1953 , 18 ( 7 ), 779 .
   Web of Science ®Google Scholar
• Percival , D. F. ; Herbst , R. M. Alkylated 5-aminotetrazoles, their preparation and properties . J. Org. Chem. 1957 , 22 , 925 .
   Web of Science ®Google Scholar
• (a) Garbrecht , W. L. ; Herbst , R. M. The synthesis of certain 5-aminotetrazole derivatives, II: The action of hydrazoic acid on monoalkylcyanamides . J. Org. Chem. 1953 , 18 ( 8 ), 1014 ; (b) Henry , R. A. ; Finnegan , W. G. ; Lieber , E. Thermal isomerization of substituted 5-aminotetrazoles . J. Am. Chem. Soc. 1954 , 76 , 88 .
   Web of Science ®Google Scholar
• Miller , A. E. ; Feenay , D. J. ; Ma , Y. ; Zarcone , L. ; Aziz , M. A. ; Magnuson , E. The synthesis of aminoiminoethanenitriles, 5-aminotetrazoles, N-cyanoguanidines, and N-hydroxyguanidines from aminoiminomethanesulfonic acids . Synth. Commun. 1990 , 20 , 217 .
   Web of Science ®Google Scholar
• (a) Batey , R. A. ; Powell , D. A. A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: A strategy for diversity amplification . Org. Lett. 2000 , 2 , 3237 ; (b) Yu , Y. ; Ostresh , J. M. ; Houghten , R. A. Solid-phase synthesis of 5-aminotetrazoles . Tetrahedron Lett. 2004 , 45 , 7787 .
   PubMed Web of Science ®Google Scholar
• (a) Das , B. ; Thirupathi , P. ; Mahender , I. ; Reddy , K. R. ; Ravikanth , B. ; Nagarapu , L. An efficient synthesis of 1,8-dioxo-octahydroxanthenes using heterogeneous catalysts . Catal. Commun. 2007 , 8 , 535 ; (b) Das , B. ; Thirupathi , P. ; Mahender , I. ; Reddy , V. S. ; Rao , Y. K. Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines . J. Mol. Catal. A: Chem. 2006 , 247 , 233 .
   Web of Science ®Google Scholar
• (a) Das , B. ; Laxminarayana , K. ; Ravikanth , B. Application of heterogeneous catalysts for an efficient synthesis of β-keto enol ethers. J. Mol. Catal. A: Chem. 2007, 271, 131; (b) Das , B. ; Damodar , K. ; Chowdhury , N. ; Kumar , R. A. Application of heterogeneous solid acid catalysts for Friedlander synthesis of quinolines. J. Mol. Catal. A: Chem. 2007, 274, 148; (c) Wang , Y. ; Sarris , K. ; Sauer , D. R. ; Djuric , S. W. An expeditious and convenient synthesis of acylsulfonamides utilizing polymer-supported reagents. Tetrahedron Lett. 2007, 48, 5181; (d) Polshettiwar , V. ; Molnár , Á. Silica-supported Pd catalysts for Heck coupling reactions. Tetrahedron 2007, 63, 6949.
   Web of Science ®Google Scholar
• (a) Ahmed , N. ; Van Lier , J. E. Silica-gel-supported TaBr5: New catalyst for the facile and rapid cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 2725 ; (b) Bandini , M. ; Luque , R. ; Budarin , V. ; Macquarrie , D. J. Aryl alkynylation versus alkyne homocoupling: Unprecedented selectivity switch in Cu, phosphine, and solvent-free heterogeneous Pd-catalysed couplings . Tetrahedron 2005 , 61 , 9860 ; (c) Ramesh , C. ; Mahender , G. ; Ravindranath , N. ; Das , B. A simple, mild, and efficient procedure for selective cleavage of prenylesters using silica-supported sodium hydrogen sulphate as a heterogenous catalyst . Tetrahedron Lett. 2003 , 44 , 1465 .
   Web of Science ®Google Scholar
• (a) Chari , M. A. ; Shobha , D. ; Mukkanti , K. Silica gel/FeCl3: An efficient and recyclable heterogenous catalyst for one-step synthesis of 4(3H)-quinazolinones under solvent-free conditions . Catal. Commun. 2007 , 7 , 787 ; (b) Dang , Q. ; Brown , B. S. ; Erion , M. D. Efficient synthesis of purine analogues: An FeCl3-SiO2-promoted cyclization reaction of 4,5-diaminopyrimidines with aldehydes leading to 6,8,9-trisubstituted purines . Tetrahedron Lett. 2000 , 41 , 6559 ; (c) Morys , P. ; Schlieper , T. Synthesis and catalytic activity of silica-supported iron(III) . J. Mol. Catal. A: Chem. 1995 , 95 , 27 ; (d) Funabiki , T. ; Ohashi , H. ; Sugimoto , T. ; Yoshida , S. Oxidation of hydroxybenzenes with oxygen catalyzed by supported metal chloride catalysts in aprotic solvents, part 1: Effects of supports and solvents on reactivity . J. Mol. Catal. 1991 , 69 , 407 ; (e) Kim , K. S. ; Song , Y. H. ; Lee , B. H. ; Hahn , C. S. Efficient and selective cleavage of acetals and ketals using ferric chloride adsorbed on silica gel . J. Org. Chem. 1986 , 51 , 404 ; (f) Fadel , A. ; Salaün , J. Anhydrous ferric chloride adsorbed on silica gel induced ring enlargement of tertiary cyclobutanols: Synthesis of isolaurolene and derivatives, campholenic ether, and (±) cuparene . Tetrahedron 1985 , 41 , 413 ; (g) Fadel , A. ; Salaün , J. Anhydrous ferric chloride dispersed on silica gel induced ring enlargement of tertiary cycloalkanols, II: A convenient homologation of cycloalkanones, preparation of spiro systems, and propella-γ-lactones . Tetrahedron 1985 , 41 , 1267 ; (h) Tal , D. M. ; Keinan , E. ; Mazur , Y. Reactions in dry media: Reactions of cholesterol and cholestanes on silica-bound ferric chloride: Cholestane- diacholestene rearrangement . Tetrahedron 1981 , 37 , 4327 ; (i) Patney , H. K. A rapid mild and efficient method of thioacetalization using anhydrous iron(III) chloride dispersed on silica gel . Tetrahedron Lett. 1991 , 32 , 2259 .
   Web of Science ®Google Scholar
• (a) Nasrollahzadeh , M. ; Bayat , Y. ; Habibi , D. ; Moshaee , S. FeCl3-SiO2 as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles via [2 + 3] cycloaddition of nitriles and sodium azide . Tetrahedron Lett. 2009 , 50 , 4435 ; (b) Kamali , T. A. ; Bakherad , M. ; Nasrollahzadeh , M. ; Farhangi , S. ; Habibi , D. Synthesis of 6-substituted imidazo[2,1-b]thiazoles via Pd/Cu-mediated Sonogashira coupling in water . Tetrahedron Lett. 2009 , 50 , 5459 .
   Web of Science ®Google Scholar
• (a) Modarresi-Alam , A. R. ; Nasrollahzadeh , M. ; Khamooshi , F. Solvent-free preparation of primary carbamates using silica sulfuric acid as an efficient reagent. Arkivoc 2007, 16, 234; (b) Modarresi-Alam , A. R. ; Khamooshi , F. ; Nasrollahzadeh , M. ; Amirazizi , H. A. Silica-supported perchloric acid (HClO4– SiO2): An efficient reagent for the preparation of primary carbamates under solvent-free conditions. Tetrahedron 2007, 63, 8723; (c) Modarresi-Alam , A. R. ; Nasrollahzadeh , M. ; Khamooshi , F. Al(HSO4)3-mediated for the preparation of primary carbamates under solvent-free conditions. Scientia Iranica 2008, 15, 452; (d) Habibi , D. ; Marvi , O. Montmorillonite KSF and montmorillonite K-10 clays as efficient catalysts for the solventless synthesis of bismaleimides and bisphthalimides using microwave irradiation. Arkivoc 2006, 13, 8; (e) Habibi , D. ; Marvi , O. Montmorillonite K-10–supported one-pot synthesis of some symmetric diimides and 3a,4,7,7a-tetrahydroisoindole-1,3-dione derivatives under solvent-free conditions using microwaves. J. Serb. Chem. Soc. 2005, 70, 579.
   Google Scholar
• Crutchley , R. J. ; Nakicki , M. L. Pentaammineruthenium(III) complexes of neutral and anionic (2,3-dichlorophenyl)cyanamide: A spectroscopic analysis of ligand to metal charge-transfer spectra . Inorg. Chem. 1989 , 28 , 1955 .
   Web of Science ®Google Scholar
• (a) Henry , R. A. ; Finnegan , W. G. ; Lieber , E. Kinetics of the isomerization of substituted 5-aminotetrazoles . J. Am. Chem. Soc. 1955 , 77 , 2264 ; (b) Garbrecht , W. L. ; Herbst , R. M. The synthesis of certain 5-aminotetrazole derivatives, I: The action of hydrazoic acid on some dialkylcyanamides . J. Org. Chem. 1953 , 18 , 1003 ; (c) Garbrecht , W. L. ; Herbst , R. M. The synthesis of certain 5- aminotetrazole derivatives, III: The synthesis of certain 5- monoalkylaminotetrazoles . J. Org. Chem. 1953 , 18 , 1022 .
   Web of Science ®Google Scholar
• (a) Schelenz , T. ; Schäfer , W. Zur physikalisch-chemischen charakterisierung von 5-amino-1-aryl-1H-tetrazolen: Elektronische molekülparameter aus der thermischen isomerisierung zu 5-arylamino-1H-tetrazolen . J. Prakt. Chem. 2000 , 342 , 197 ; (b) Katritzky , A. R. ; Jain , R. ; Petrukhin , R. ; Denisenko , S. ; Schelenz , T. Qsar correlations of the algistatic activity of 5-amino-1-aryl-1H-tetrazoles . SAR QSAR Environ. Res. 2001 , 12 , 259 .
   Google Scholar
• (a) Goljer , I. ; Svetlik , J. ; Hrusovsky , I. 13C-NMR of substituted tetrazoles . Monatsh. Chem. 1983 , 114 , 65 .
   Web of Science ®Google Scholar