H₁₄[NaP₅W₃₀O₁₁₀] as a Heterogeneous Recyclable Catalyst for the Synthesis of 6,8-Dimethyl-3-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiazepine Derivatives

REFERENCES

• Eweiss , N. F. ; Bahajaj , A. A. Synthesis of heterocycles, part VII: Synthesis and antimicrobial activity of some 7H-s-triazolo[3,4-b][1,3,4]thiadiazine and s-triazolo[3,4-b][1,3,4]thiadiazole derivatives . J. Heterocycl. Chem. 1987 , 24 , 1173 – 1182 .
   Google Scholar
• (a) Heravi , M. M. ; Kivanloo , A. ; Rahimzadeh , M. ; Bakavoli , M. ; Ghassemzaeh , M. Pd–Cu–catalyzed heterocyclization during Sonogashira coupling: Synthesis of 3-benzylthiazolo[3,2-a]benzimidazole . Tetrahedron Lett. 2004 , 45 , 5747 – 5749 ; (b) Heravi , M. M. ; Kivanloo , A. ; Rahimzadeh , M. ; Bakavoli , M. ; Ghassemzaeh , M. ; Neumüller , B. Regioselective synthesis of 6-benzylthiazolo[3,2-b]1,2,4-triazoles during Sonogashira coupling . Tetrahedron Lett. 2005 , 46 , 1607 – 1610 .
   Web of Science ®Google Scholar
• Tiwari , N. ; Singh , K. ; Nizamuddin , N. Synthesis of [1,2,4]-triazolo[3,4-b][1,3,4]thiadiazepines and [1,2,4]triazolo[3,4-b][1,3,4]benzothiadiazocines . Indian J. Heterocycl. Chem. 1993 , 2 , 195 – 198 .
   Google Scholar
• Mizuno , N. ; Misono , M. Heteropolyanions in catalysis . J. Mol. Catal. 1994 , 86 , 319 – 342 .
   Google Scholar
• Izumi , Y. ; Urabe , K. ; Onaka , M. Zeolite, Clay, and Heteropoly Acid in Organic Reactions ; Kadansha : Tokyo , 1992 .
   Google Scholar
• Kozhevinkov , I. V. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions . Chem. Rev. 1998 , 98 , 171 – 198 .
   PubMedGoogle Scholar
• (a) Kozhevinkov , I. V. Catalysis for fine chemicals . In Catalysis by Polyoxometalates ; John Wiley and Sons : New York , 2002 ; (b) Misono , M. ; Nojiri , N. Recent progress in catalytic technology in Japan. Appl. Catal. 1990, 64, 1–30 .
   Google Scholar
• Timofeeva , M. N. Acid catalysis by heteropoly acids . Appl. Catal. 2003 , 256 , 19 – 35 .
   Google Scholar
• Harrup , M. K. ; Hill , C. L. Polyoxometalate catalysis of the aerobic oxidation of hydrogen sulfide to sulfur . Inorg. Chem. 1994 , 33 , 5448 – 5455 .
   Web of Science ®Google Scholar
• (a) Bamoharram , F. F. ; Heravi , M. M. ; Roshani , M. ; Jahangir , M. ; Gharib , A. Preyssler catalyst, [NaP5W30O110]14−: A green, efficient, and reusable catalyst for esterification of salicylic acid with aliphatic and benzylic alcohols . Appl. Catal. 2006 , 302 , 42 – 47 ; (b) Bamoharram , F. F. ; Heravi , M. M. ; Roshani , M. ; Gharib , A. ; Jahangir , M. A catalytic method for synthesis of γ-butyrolactone, ϵ-caprolactone, and 2-cumaranone in the presence of Preyssler's anion, [NaP5W30O110]14−, as a green and reusable catalyst . J. Mol. Catal. 2006 , 252 , 90 – 95 .
   Google Scholar
• (a) Heravi , M. M. ; Motamedi , R. ; Seifi , N. ; Bamoharram , F. F. Catalytic synthesis of 6-aryl-1H-pyrazolo[3,4-d]pyrimidin-4[5H]-ones by heteropolyacid: H14[NaP5W30O110] and H3PW12O40 . J. Mol. Catal. 2006, 249, 1–3; (b) Heravi , M. M. ; Bakhtiari , K. ; Bamoharram , F. F. 12-Molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones. Catal. Commun. 2006, 7, 373–376; (c) Bamoharram , F. F. ; Heravi , M. M. ; Roshani , M. ; Takakoli , N. N-Oxidation of pyridine carboxylic acids using hydrogen peroxide catalyzed by a green heteropolyacid catalyst: Preyssler's anion, [NaP5W30O110]14− . J. Mol. Catal. 2006, 252, 219–225; (d) Heravi , M. M. ; Bakhtiari , K. ; Bamoharram , F. F. An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdophosphoric acid. Catal. Commun. 2006, 7, 499–501.
   Web of Science ®Google Scholar
• Lefebvre , F. 31P MAS NMR study of H3PW12O40 supported on silica: Formation of (≡ )(H2PW12 ) . J. Chem. Soc., Chem. Commun. 1992 , 10 , 756 – 757 .
   Google Scholar
• Kozhevnikov , I. V. ; Kloetstra , K. R. ; Sinnema , A. ; Zandbergen , H. W. ; Van Bekkum , H. Study of catalysts comprising heteropoly acid H3PW12O40 supported on MCM-41 molecular sieve and amorphous silica . J. Mol. Catal. 1996 , 114 , 287 – 298 .
   Web of Science ®Google Scholar
• Alizadeh , M. H. ; Razavi , H. ; Bamoharram , F. F. ; Hassanzadeh , M. K. Novel catalytic acetylation of alcohols with Preyssler's anion, [NaP5Wa30O110]14−1 . Kinet. Catal. 2003 , 44 , 524 – 528 .
   Web of Science ®Google Scholar
• (a) Sharfi , T. ; Heravi , M. M. ; Ghassemzadeh , M. ; Neumuller , B. Synthesis, characterization, and crystal structure of the dimeric silver(I) complex containing 4-amino-5-methyl-2H-1,2,4-triazole-3(4H)-thione . Z. Anorg. Allg. Chem. 2005 , 631 , 2297 – 2299 ; (b) Ghassemzadeh , M. ; Tabatabaee , M. ; Pouramin , M. M. ; Heravi , M. M. ; Eslami , A. ; Neumuller , B. Synthesis and characterization of a novel 1,2,4-thiotriazine derivative (CAMTTO), and copper(I) and silver(I) complexes thereof (CAMTTO = {(4-[(4-chlorobenzylidene)-amino]-6-methyl-3-thioxo-[1,2,4]-triazin-3,4-dihydro(2H)-5-one)} . Z. Anorg. Allg. Chem. 2006 , 632 , 786 – 792 .
   Google Scholar