Reactivity of Benzofuran Derivatives

REFERENCES

• Rao , G. K. ; Venugopala , K. N. ; Pai , P. N. S. Novel Schiff bases of 4-hydroxy 6-carboxhydrazino benzofuran analogs: Synthesis and pharmacological study . J. Pharmacol. Toxicol. 2007 , 2 , 481 – 488 .
   Google Scholar
• Koca , M. ; Servi , S.; Kirilmis C. ; Ahmedzade , M. ; Kazaz , C. ; Özbek , B. ; Ötük , G. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1: Synthesis and antimicrobial activity of (benzofuran-2-yl) (3-phenyl-3-methylcyclobutyl) ketoxime derivatives . Eur. J. Med. Chem. 2005 , 40 , 1351 – 1358 .
   PubMed Web of Science ®Google Scholar
• Pieters , L. ; Dyck , S. V. ; Gao , M. ; Bai , R. ; Hamel , E. ; Vlietinck , A. ; Lemière , G. Synthesis and biological evaluation of dihydrobenzo-furan lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization . J. Med. Chem. 1999 , 42 , 5475 – 5481 .
   PubMed Web of Science ®Google Scholar
• Banskota , A. H. ; Tezuka , Y. ; Midorikawa , K. ; Matsushige , K. ; Kadota , S. Two novel cytotoxic benzofuran derivatives from Brazilian propolis . J. Nat. Prod. 2000 , 63 , 1277 – 1279 .
   PubMed Web of Science ®Google Scholar
• Dawood , K. M. ; Abdel-Gawad , H. ; Rageb , E. A. ; Ellithey , M. ; Mohamed , H. A. Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole- and benzofuran-based heterocycles. Bioorg. Med. Chem. 2006, 14, 3672–3680.
   PubMed Web of Science ®Google Scholar
• Tsujihara , K. ; Hongu , M. ; Saito , K. ; Kawanishi , H. ; Kuriyama , K. ; Matsumoto , M. ; Oku , A. ; Ueta , K. ; Tsuda , M. ; Saito , A. Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents, 4: Synthesis and pharmacological properties of 4-dehydroxyphlorizin derivatives substituted on the B ring . J. Med. Chem. 1999 , 42 , 5311 – 5324 .
   PubMed Web of Science ®Google Scholar
• Liao , Y. ; Kozikowski , A. P. ; Guidotti , A. ; Costa , E. Synthesis and pharmacological evaluation of benzofuran-acetamides as “antineo-phobic” mitochondrial DBI receptor complex ligands . Bioorg. Med. Chem. Lett. 1998 , 8 , 2099 – 2102 .
   PubMed Web of Science ®Google Scholar
• Ono , M. ; Kawashima , H. ; Nonaka , A. ; Kawai , T. ; Haratake , M. ; Mori , H. ; Kung , M. ; Kung , H. F. ; Saji , H. ; Nakayama , M. Novel benzofuran derivatives for PET imaging of β-amyloid plaques in Alzheimer's disease brains . J. Med. Chem. 2006 , 49 , 2725 – 2730 .
   PubMed Web of Science ®Google Scholar
• Manish , D. ; Tripathi , B. K. ; Tamrakar , A. K. ; Srivastava , A. K. ; Kumar , B. ; Goel , A. Synthesis of benzofuran-scaffold-based potential PTP-1B inhibitors . Bioorg. Med. Chem. 2007 , 15 , 727 – 734 .
   PubMed Web of Science ®Google Scholar
• Sofuoglu , M. ; Portoghese , P. S. ; Takemori , A. E. Differential antagonism of delta opioid agonists by naltrindole and its benzofuran analog (NTB) in mice: Evidence for delta opioid receptor subtypes . J. Pharmacol. Exp. 1991 , 257 , 676 – 680 .
   PubMed Web of Science ®Google Scholar
• Naccarelli , G. V. ; Wolbrette , D. L. ; Patel , H. M. ; Luck , J. C. Amiodarone: Clinical trials . Curr. Opin. Cardiol. 2000 , 15 , 64 – 72 .
   PubMed Web of Science ®Google Scholar
• Kathofer , S.; Thomas D. ; Karle , C. A. The novel antiarrhythmic drug dronedarone: Comparison with amiodarone . Cardiovascular Drug Rev. 2005 , 23 , 217 – 230 .
   PubMed Web of Science ®Google Scholar
• Fleming , I. In Frontier Orbitals and Organic Chemical Reactions ; Wiley : New York , 1976 ; p. 58 .
   Google Scholar
• Carlsson , B. ; Singh , B. N. ; Temciuc , M. ; Nilsson , S. ; Li , Y.-L. ; Mellin , C. ; Malm , J. Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone . J. Med. Chem. 2002 , 45 , 623 – 630 .
   PubMed Web of Science ®Google Scholar
• Black , D. S. ; Craig , D. C. ; Kumar , N. ; Rezaie , R. Acid-catalysed reactions of activated benzofuranylmethanols: Formation of calixbenzofurans . Tetrahedron 2002 , 58 , 5125 – 5134 .
   Web of Science ®Google Scholar
• Yang , Z. ; Liu , H. B. ; Lee , C. M. ; Chang , H. M. ; Wong , H. N. C. Regioselective introduction of carbon-3-substitutes to 5-alkyl-7-methoxy-2-phenylbenzo[b] furans: Synthesis of a novel adenosine A1 receptor ligand and its derivatives . J. Org. Chem. 1992 , 57 , 7248 .
   Web of Science ®Google Scholar
• Abdelhamid , A. O. ; Fahmi , A. A. ; Alsheflo , A. A. M. Convenient synthesis of some new pyrazolo[5,1-c]triazines, isoxazolo[3,4-d] pyrimidine, and pyridine derivatives containing benzofuran moiety . Eur. J. Chem. 2012 , 3 , 129 – 137 .
   Google Scholar
• Wrobel , J. ; Sredy , J. ; Moxham , C. ; Dietrich , A. ; Li , Z. ; Sawicki , D. R.; Eestaller, L. S.; Wu, L.; Katz, A.; Sullivan, D.; Tio, C.; Zhang, Z.-Y. PTP1B inhibition and antihyperglycemic activity in the ob/ob mouse model of novel 11-arylbenzo[b]naphtho[2,3-d]furans and 11-arylbenzo[b]naphtho[2,3-d]thiophenes . J. Med. Chem. 1999 , 42 , 3199 – 3202 .
   PubMed Web of Science ®Google Scholar
• Yamaguchi , T. ; Irie , M. Photochromism of bis (2-alkyl-1-benzofuran-3-yl)perfluorocyclopentene derivatives . J. Org. Chem. 2005 , 70 , 10323 – 10328 .
   PubMed Web of Science ®Google Scholar
• Bach , T. ; Bartels , M. Synthesis and characterization of iodine-123-labeled 2-beta-carbomethoxy-3beta-(4′-((Z)-2-iodoethenyl)-phenyl)nortropane: A ligand for in vivo imaging of serotonin transporters by single-photon-emission tomography . Synthesis 2003 , 46 , 925 – 935 .
   Google Scholar
• Dawood , K. M. ; Fuchigami , T. The first solid-phase synthesis of oligomeric a-aminooxy peptides . Synlett 2003 , 325 – 328 .
   Web of Science ®Google Scholar
• Shouzhi , P. ; Renjie , W. ; Liu , G. ; Liu , W. ; Cui , S. ; Yan , P. Photochromism of new unsymmetrical diarylethene derivatives bearing both benzofuran and thiophene moieties . Dyes Pigm. 2012 , 94 , 195 – 206 .
   Web of Science ®Google Scholar
• Zhang , W. ; Wang , P. G. Ytterbium(III) trifluoromethanesulfonate–catalyzed electrophilic aromatic substitution with glyoxalate and lipase-mediated product resolution: A convenient route to optically active aromatic alpha-hydroxy esters. J. Org. Chem. 2000, 65, 4732–4735.
   PubMed Web of Science ®Google Scholar
• Kraus , G. A. ; Wei , J. Phytochemical medicinal agents: A quinone-based route to pterocarpins . Tetrahedron Lett. 2005 , 46 , 7511 – 7513 .
   PubMed Web of Science ®Google Scholar
• Wells , G. ; Berry , J. M.; Bradshaw, T. D.; Burger, A. M.; Seaton, A.; Wang, B.; Westwell, A. D.; Stevens, M. F. G. 4-Substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines . J. Med. Chem. 2003 , 46 , 532 – 541 .
   PubMed Web of Science ®Google Scholar
• Katrizky , A. R. ; Fali , C. N. ; Li , J. General synthesis of polysubstituted- benzo[b]furans . J. Org. Chem. 1997 , 62 , 8205 – 8209 .
   PubMed Web of Science ®Google Scholar
• Rangaswamy , J. ; Kumar , H. V. ; Harini , S. T. ; Naik , N. Synthesis of benzofuran-based 1,3,5-substituted pyrazole derivatives as a new class of potent antioxidants and antimicrobials: A novel accost to amend biocompatibility . Bioorg. Med. Chem. Lett. 2012 , 22 , 4773 – 4777 .
   PubMed Web of Science ®Google Scholar
• Fuerst , D. E. ; Stoltz , B. M. ; Wood , J. L. Synthesis of C (3) benzofuran-derived bisaryl quaternary centers: Approaches to diazonamide A . Org. Lett. 2000 , 2 , 3521 – 3523 .
   PubMed Web of Science ®Google Scholar
• Davies , H. M. L. Dirhodium tetra(N-arylsulfonylprolinates) as chiral catalysts for asymmetric transformations of vinyl- and aryl-diazoacetates . Eur. J. Org. Chem. 1999 , 10 , 2445 – 2693 .
   Google Scholar
• Hwu , J. R. ; Chen , K.-L. ; Ananthan , S. ; Patel , H. V. Ultrasonic nitration of allylsilanes by use of sodium nitrite and ceric ammonium nitrate . Organometallics 1996 , 15 , 499 – 505 .
   Web of Science ®Google Scholar
• Sauter , M. ; Adam , W. Oxyfunctionalization of benzofurans by singlet oxygen, dioxiranes, and peracids: Chemical model studies for the DNA-damaging activity of benzofuran dioxetanes (oxidation) and epoxides (alkylation) . Acc. Chem. Res. 1995 , 28 , 289 .
   Web of Science ®Google Scholar
• Alvarez , R. G.; Hunter, I. S.; Suckling, C. J.; Thomas, M.; Vitinius, U. A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase . Tetrahedron 2001 , 57 , 8581 – 8587 .
   Web of Science ®Google Scholar
• Yus , M. ; Foubelo , F. ; Ferrández , J. V. ; Bachki , A. Reductive lithiation of cyclic benzofused ethers: A source of oxygen-functionalised organolithium compounds . Tetrahedron 2002 , 58 , 4907 – 4915 .
   Web of Science ®Google Scholar
• Yus , M. ; Foubelo , F. ; Ferrández , J. V. Stereoselective reductive opening of 2,3-benzofuran: A two-step synthesis of 2H-chromenes including deoxycordiachromene . Eur. J. Org. Chem. 2001 , 2809 – 2813 .
   Web of Science ®Google Scholar
• Juhász , L. ; Szilágyi , L. ; Antus , S. ; Visy , J. ; Zsila , F. ; Simonyi , M. New insight into the mechanism of hypervalent iodine oxidation of flavanones . Tetrahedron 2002 , 58 , 4261 – 4265 .
   Web of Science ®Google Scholar
• Mévellec , V. ; Roucoux , A. Nanoheterogeneous catalytic hydrogenation of N-, O-, or S-heteroaromatic compounds by re-usable aqueous colloidal suspensions of rhodium(0) . Inorg. Chim. Acta 2004 , 357 , 3099 .
   Web of Science ®Google Scholar
• Graham , S. L. ; Hoffman , J. M. ; Gautheron , P. ; Michelson , S. R. ; Scholz , T. H. ; Schwarm , H. ; Shepard , K. L. ; Smith , A. M. ; Smith , R. L. ; et al. . Topically active carbonic anhydrase inhibitors, 3: Benzofuran- and indole-2-sulfonamides . J. Med. Chem. 1990 , 33 , 749 – 754 .
   PubMed Web of Science ®Google Scholar
• Zhang , H. ; Larock , R. C. Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes . J. Org. Chem. 2002 , 67 , 7048 – 7056 .
   PubMed Web of Science ®Google Scholar
• Gissot , A. ; Becht , J.-M. ; Desmurs , J. R. ; Pévère , V. ; Wagner , A. ; Mioskowski , C. Directed ortho-metalation, a new insight into organosodium chemistry . Angew. Chem., Int. Ed. 2002 , 41 , 340 – 343 .
   PubMed Web of Science ®Google Scholar
• Huang , X.-T. ; Long , Z.-Y. ; Chen , Q.-Y. Fluoroalkylation of aromatic compounds with per(poly)fluoroalkyl chlorides initiated by sodium dithionate in DMSO . J. Fluorine Chem. 2001 , 111 , 107 – 113 .
   Web of Science ®Google Scholar
• Inoue , M. ; Carson , M. W. ; Frontier , A. J. ; Danishefsky , S. J. Total synthesis and determination of the absolute configuration of frondosin B. J. Am. Chem. Soc. 2001, 123, 1878–1889.
   PubMed Web of Science ®Google Scholar
• Hughes , C. C. ; Trauner , D. Palladium-catalyzed couplings to nucleophilic heteroarenes: The total synthesis of (−)-frondosin B . Tetrahedron 2004 , 60 , 9675 – 9686 .
   Web of Science ®Google Scholar
• Bach , T. ; Bartels , M. Regioselective C-C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans . Synthesis 2003 , 925 – 939 .
   Web of Science ®Google Scholar
• Yates , B. F. Review article: 11 computational organic chemistry . Annu. Rep. Prog. Chem., Sect. B 2004 , 100 , 251 – 283 .
   Google Scholar
• Dyker , G. ; Hildebrandt , D. ; Liu , J. ; Merz , K. Gold(III) chloride–catalyzed domino processes with isobenzopyrylium cation intermediates . Angew. Chem., Int. Ed. 2003 , 42 , 4399 .
   PubMed Web of Science ®Google Scholar
• Gonzalez-Gomez , J. C. ; Santana , L. ; Uriarte , E. Uriarte, E . Tetrahedron 2005 , 61 , 4805 – 4810 .
   Web of Science ®Google Scholar
• Simon , O. ; Reux , B. ; La Clair , J. J. ; Lear , M. J. Total synthesis confirms laetirobin as a formal Diels–Alder adduct . Chem. Asian J. 2010 , 5 , 342 – 351 .
   PubMed Web of Science ®Google Scholar
• Klymchenko , A. S.; Mély, Y. 7-(2-Methoxycarbonylvinyl)-3-hydroxy chromones: New dyes with red-shifted dual emission . Tetrahedron Lett. 2004 , 45 , 8391 – 8394 .
   Web of Science ®Google Scholar
• Campiani , G. ; Butini , S. ; Trotta , F. ; Fattorusso , C. ; Catalanotti , B. ; Aiello , F. ; Gemma , S. ; Nacci , V. ; Novellino , E. ; Stark , J. A. ; Cagnotto , A. ; Fumagalli , E. ; Carnovali , F. ; Cervo , L. ; Mennini , T. Synthesis and pharmacological evaluation of potent and highly selective D3 receptor ligands: Inhibition of cocaine-seeking behavior and the role of dopamine D3/D2 receptors . J. Med. Chem. 2003 , 46 , 3822 – 3839 .
   PubMed Web of Science ®Google Scholar
• Sakamoto , M. ; Kinbara , A. ; Yagi , T. ; Mino , T. ; Yamaguchi , K. ; Fujita , T. A novel photocycloaddition of substituted pyridines with benzofuran . Chem. Commun. 2000 , 1201 – 1202 .
   Web of Science ®Google Scholar
• D'Auria , M. ; Emanuele , L. ; Racioppi , R. Diastereoselectivity in the Paternò–Büchi reaction on furan derivatives . Tetrahedron Lett. 2004 , 45 , 3877 – 3880 .
   Web of Science ®Google Scholar
• Zhang , Y. ; Xue , J. ; Gao , Y. ; Fun , H.-K. ; Xu , J.-H. Photoinduced [2 + 2] cycloadditions (the Paterno–Büchi reaction) of 1-acetylisatin with enol ethers regioselectivity, diastereoselectivity, and acid-catalysed transformations of the spirooxetane products . J. Chem. Soc., Perkin Trans. 1 2002 , 345 – 353 .
   Google Scholar
• Nishio , T. ; Shiwa , K. ; Sakamoto , M. Photoaddition reactions of benzoxazole-2(3H)-thiones to cycloalkenes and heteroaromatics . Helv. Chim. Acta 2003 , 86 , 3255 – 3264 .
   Web of Science ®Google Scholar
• Ashraf , M. A. ; Jones , M. A. ; Kelly , N. E. ; Mullaney , A. ; Snaith , J. S. ; Williams , I. Synthesis and photolysis studies of carboxylic esters of 2-hydroxy-1,2,2-triphenylethanone: A novel tandem photocyclisation . Tetrahedron Lett. 2003 , 44 , 3151 – 3154 .
   Web of Science ®Google Scholar