Phosphomolybdic Acid/SiO₂ as Heterogeneous Solid Acid Catalyst for the Rapid Synthesis of N-Substituted Pyrroles

REFERENCES

• Lehuedu , J. ; Fauconneau , B. ; Barrier , L. ; Ourakow , M. ; Piriou , A. ; Vierfond , J. M. Synthesis and antioxidant activity of new tetraarylpyrroles . Eur. J. Med. Chem. 1999 , 34 , 991 – 996.
   PubMedGoogle Scholar
• Hayakawa , Y. ; Kawasaki , K. ; Seto , H . Structure of a new antibiotic roseophilin . Tetrahedron Lett. 1992 , 33 , 2701 – 2704.
   Web of Science ®Google Scholar
• Dong , Y. ; Naranjan , N. ; Ablaza , S. L. ; Yu , S. X. ; Bolvig , S. ; Forsyth , D. A. ; Le Quesne , P. W. Quararibea metabolites, 4: Total synthesis and conformational studies of (±)-funebrine and (±)-funebral . J. Org. Chem. 1999 , 64 , 2657 – 2666.
   Google Scholar
• Arrowsmith , J. ; Jennings , S. A. ; Clark , A. S. ; Stevens , M. F. G. Antitumor imidazotetrazines, 41: Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs . J. Med.Chem. 2002 , 45 , 5458 – 5470.
   PubMed Web of Science ®Google Scholar
• Haubmann , C. ; Huebner , H. ; Gmeiner , P. Piperidinylpyrroles: Design, synthesis and binding properties of novel and selective dopamine D4 receptor ligands. Bioorg . Med. Chem. Lett. 1999 , 9 , 3143 – 3146.
   PubMed Web of Science ®Google Scholar
• Robertson , J. ; Hatley , R. J. D. ; Watkin , D. J. Preparation of the tricyclic ketopyrrole core of roseophilin by radical macrocyclisation and Paal–knorr condensation . J. Chem. Soc., Perkin Trans. 2000 , 1 , 3389 – 3396.
   Google Scholar
• Joule , J. A. ; Mills , K. ; Smith , G. F. Heterocyclic Chemistry, , 4th ed. , Blackwell Science : Oxford , 2000.
   Google Scholar
• Jones , R. A. ; Bean , G. P. The Chemistry of Pyrroles ; Academic Press : London , 1977.
   Google Scholar
• Alongi , M. ; Minetto , G. ; Taddei , M. New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds . Tetrahedron Lett. 2005 , 46 , 7069 – 7072.
   Google Scholar
• Thompson , R. B. Foundations for blockbuster drugs in federally sponsored research . FASEB J. 2001 , 15 , 1671 – 1676.
   PubMed Web of Science ®Google Scholar
• Cozzi , P. ; Mongelli , N. Cytotoxics derived from distamycin a and congeners . Curr. Pharm. Des. 1998 , 4 , 181 – 201.
   PubMed Web of Science ®Google Scholar
• Furstner , A. ; Szillat , H. ; Gabor , B. ; Mynott , R. Platinum- and acid-catalyzed enyne metathesis reactions: Mechanistic studies and applications to the syntheses of streptorubin b and metacycloprodigiosin . J. Am. Chem. Soc. 1998 , 120 , 8305 – 8314.
   Google Scholar
• Gilchrist , T. L. Synthesis of aromatic heterocycles . J. Chem. Soc., Perkin Trans. 1998 , 1 , 615 – 628 , and references cited therein.
   Google Scholar
• Yu , S.-X. ; Le Quesne , P. W. Quararibea metabolites. 3. Total synthesis of (±)-funebral, a rotationally restricted pyrrole alkaloid, using a novel Paal-Knorr reaction . Tetrahedron Lett. 1995 , 36 , 6205 – 6208.
   Web of Science ®Google Scholar
• Dieter , R. K. ; Yu , H. A facile synthesis of polysubstituted pyrroles . Org. Lett. 2000 , 2 , 2283 – 2286.
   PubMed Web of Science ®Google Scholar
• Periasamy , M. ; Srinivas , G. ; Bharati , P. Conversion of aryl methyl ketimines to 2,5-diarylpyrroles using TiCl4/Et3N . J. Org. Chem. 1999 , 64 , 4204 – 4205.
   Web of Science ®Google Scholar
• Azizian , J. ; Karimi , A. R. ; Kazemizadeh , Z. ; Mohammadi , A. A. A novel one-pot synthesis of some new interesting pyrrole derivatives. J. Org. Chem. 2005, 70, 1471–1473.
   PubMed Web of Science ®Google Scholar
• Banik , B. K. ; Cardona , M. Bismuth nitrate–catalyzed novel synthesis of pyrrole-substituted indolinones . Tetrahedron Lett. 2006 , 47 , 7385 – 7387.
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Jain , R. ; Suresh Reddy , C. Dy(OTf)3 as a versatile catalyst for the synthesis of 3-pyrrolyl-indolinones and pyrrolyl-indeno[1,2-b]quinoxalines . Tetrahedron Lett. 2007 , 48 , 3295 – 3298.
   Google Scholar
• Misono , M. ; Ono , I. ; Koyano , G. ; Aoshima , A. Heteropolyacids: Versatile green catalysts usable in a variety of reaction media . Pure Appl. Chem. 2000 , 72 , 1305 – 1311.
   Web of Science ®Google Scholar
• Wilson , K. ; Clark , J. H. Solid acids and their use as environmentally friendly catalysts in organic synthesis . Pure Appl. Chem. 2000 , 72 , 1313 – 1319.
   Web of Science ®Google Scholar
• Kozhevnikov , I. V. Catalysis by heteropoly acids and multicomponent polyoxo-metalates in liquid-phase reactions . Chem. Rev. 1998 , 98 , 171 – 198.
   PubMed Web of Science ®Google Scholar
• Mizuno , N. ; Misono , M. Heterogeneous catalysis . Chem. Rev. 1998 , 98 , 199 – 218.
   PubMed Web of Science ®Google Scholar
• Saidi , M. R. ; Torkiyan , L. ; Azizi , N. Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids . Org. Lett. 2006 , 8 , 2079 – 2082.
   Google Scholar
• Izumi , Y. ; Urabe , K. ; Onaka , M. Zeolite, Clay and Heteropoly Acid in Organic Reactions ; Kodansha/VCH : Tokyo , 1992 ; p. 99.
   Google Scholar
• Baskaran , S. ; Kumar , G. D. K. Heteropoly acid as a novel nitrene transfer agent: A facile and practical aziridination of olefins with Chloramine-T . Chem. Comm. 2004 , 1026 – 1027.
   Google Scholar
• Kishore Kumar , G. D. ; Baskaran , S. A facile, catalytic, and environmentally benign method for selective deprotection of tert-butyldimethylsilyl ether mediated by phosphomolybdic acid supported on silica gel . J. Org. Chem. 2005 , 70 , 4520 – 4523.
   PubMed Web of Science ®Google Scholar
• Kozhevnikova , E. F. ; Derouane , E. G. ; Kozhevnikov , I. V. Heteropoly acid as a novel efficient catalyst for Fries rearrangement . Chem. Commun. 2002 , 1178 – 1179.
   Google Scholar
• Yadav , J. S. ; Satyanarayana , M. ; Balanarsaiah , E. ; Raghavendra , S. Phosphomolybdic acid supported on silica gel: A mild, efficient and reusable catalyst for the synthesis of 2,3-unsaturated glycopyranosides by Ferrier rearrangement . Tetrahedron Lett. 2006 , 47 , 6095 – 6098.
   Web of Science ®Google Scholar