Efficient Synthesis of a Benzo[b]furan Building Block

REFERENCES

• Shimazu , S. ; Takahata , K. ; Katsuki , H. ; Tanigawa , A. ; Yoneda , F. ; Knoll , J. ; Akaike , A. (−)-1-(Benzofuran-2-yl)-2-propylaminopentane enhances locomotor activity in rats due to its ability to induce dopamine release . Eur. J. Pharm. 2001 , 421 , 181 – 189 .
   PubMed Web of Science ®Google Scholar
• Singh , B. N. ; Connolly , S. J. ; Crijns , H. J. ; Roy , D. ; Kowey , P. R. ; Capucci , A. ; Radzik , D. ; Aliot , E. M. ; Hohnloser , S. H. Dronedarone for maintenance of sinus rhythm in atrial fibrillation or flutter . New Engl. J. Med. 2007 , 357 , 987 – 989 .
   PubMed Web of Science ®Google Scholar
• Rosenbaum , M. B. ; Chiale , P. A. ; Haedo , A. ; Lazzari , J. O. ; Elizari , M. V. Ten years of experience with amiodarone . Am. Heart J. 1983 , 106 , 957 – 964 .
   PubMed Web of Science ®Google Scholar
• Fedi , V. ; Altamura , M. ; Catalioto , R.-M. ; Giannotti , D. ; Giolitti , A. ; Giuliani , S. ; Guidi , A. ; Harmat , N. J. S. ; Lecci , A. ; Meini , S. ; Nannacini , R. ; Pasqui , F. ; Tnamontana , M. ; Triolo , A. ; Maggi , C. A. Discovery of a new series of potent and selective linear tachykinin NK2 receptor antagonists . J. Med. Chem. 2007 , 50 , 4793 – 4478 .
   PubMedGoogle Scholar
• Masabuchi , M. ; Ebiike , H. ; Kawasaki , K. ; Sogabe , S. ; Morikami , K. ; Shiratori , Y. ; Tsujii , T. ; Fujii , T. ; Sakata , K. ; Hayase , M. ; Shindoh , H. ; Aoki , Y. ; Ohtsuka , T. ; Shimma , N. Synthesis and biological activities of benzofuran antifungal agents targeting fungal N-myristoyltransferase . Bioorg. Med. Chem. 2003 , 11 , 4463 – 4478 .
   PubMedGoogle Scholar
• For reviews of benzo[b]furan syntheses, see (a) Hou , X.-L. ; Yang , Z. ; Wong , H. N. C. Five-membered ring systems: Furans and benzofurans . Prog. Heterocycl. Chem. 2003 , 15 , 167 – 205 ; (b) McCallion , G. D. Benzo[b]furans: An investigation into natural products, bioactivity, and synthesis . Curr. Org. Chem. 1999 , 3 , 67 – 76 ; (c) Zeni , G. ; Larock , R. C. Synthesis of heterocycles via palladium π-olefin and π-alkyne chemistry . Chem. Rev. 2004 , 104 , 2285 – 2310 .
   Google Scholar
• For selected recent syntheses, see (a) Kuman , M. P. ; Liu , R.-S. Zn(OTf)2-catalyzed cyclization of propargyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms . J. Org. Chem. 2006 , 71 , 4951 – 4955 ; (b) Yue , D. ; Yao , T. ; Larock , R. C. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization . J. Org. Chem. 2005 , 70 , 10292 – 10296 ; (c) Nakamura , I. ; Mizushima , Y. ; Yamamoto , Y. Synthesis of 2,3-disubstituted benzofurans by platinum−olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals . J. Am. Chem. Soc. 2005 , 127 , 15022 – 15023 ; (d) Chen , C. ; Dormer , P. G. Synthesis of benzo[b]furans via CuI-catalyzed ring closure . J. Org. Chem. 2005 , 70 , 6964 – 6967 ; (e) Cruz , M. del C. ; Tamariz , J. Captodative olefins: Methyl 2-aryloxy-3-dimethylaminopropenoates and their application in a new synthesis of benzofurans . Tetrahedron Lett. 2004 , 45 , 2377 – 2380 ; (f) Thielges , S. ; Meddah , E. ; Bisseret , P. ; Eustache , J. New synthesis of benzo[b]furan and indole derivatives from 1,1-dibromo-1-alkenes using a tandem Pd-assisted cyclization–coupling reaction . Tetrahedron Lett. 2004 , 45 , 907 – 910 .
   PubMedGoogle Scholar
• (a) Neumann , W. P. ; Uzick , W. ; Zarkadis , A. K. Sterically hindered free radicals, 14: Substituent-dependent stabilization of para-substituted triphenylmethyl radicals . J. Am. Chem. Soc. 1986 , 108 , 3762 – 3770 ; (b) DeGraw , J. I. ; Christie , P. H. ; Colwell , W. T. ; Sirotnak , F. M. Synthesis and antifolate properties of 5,10-ethano-5,10-dideazaaminopterin . J. Med. Chem. 1992 , 35 , 320 – 324 ; (c) Taylor , E. C. ; Hu , B. A Fischer-indole approach to pyrrolo[2,3-d]pyrimidines . Heterocycles 1996 , 323 – 338 ; (d) Newman , W. P. ; Penenory , A. ; Stewen , U. ; Lehnig , M. Sterically hindered free radicals, 18: Stabilization of free radicals by substituents as studied by using triphenylmethyls . J. Am. Chem. Soc. 1989 , 15 , 5845 – 5851 ; (e) Stewen , U. ; Lehnig , M. ENDOR-untersuchungen zur capto-dativen stabilisierung phenoxysubstituierter triphenylmethylradikale . Chem. Ber. 1989 , 122 , 2319 – 2322 ; (f) Frye , S. V. ; Johnson , M. C. ; Valvano , N. L. Synthesis of 2-aminobenzophenones via rapid halogen–lithium exchange in the presence of a 2-amino-N-methoxy-N-methylbenzamide . J. Org. Chem. 1991 , 56 , 3750 – 3752 ; (g) McBriar , M. D. ; Guzik , H. ; Xu , R. ; Paruchova , J. ; Li , S. ; Palani , A. ; Clader , J. W. ; Greenlee , W. J. ; Hawes , B. E. ; Kowalski , T. J. ; O'Neill , K. ; Spar , B. ; Weig , B. Discovery of bicycloalkyl urea melanin concentrating hormone receptor antagonists: Orally efficacious antiobesity therapeutics . J. Med. Chem. 2005 , 48 , 2274 – 2277 ; (h) Alberati , D. ; Hainzl , D. ; Jolidon , S. ; Krafft , E. A. ; Kurt , A. ; Maier , A. ; Pinard , E. ; Thomas , A. W. ; Zimmerli , D. Discovery of 4-substituted-8-(2-hydroxy-2-phenylcyclohexyl)-2,8-diaza-spiro[4.5]decan-1-one as a novel class of highly selective GlyT1 inhibitors with improved metabolic stability . Bioorg. Med. Chem. Lett. 2006 , 16 , 4311 – 4315 .
   Google Scholar
• Ng , H. P. ; May , K. ; Bauman , J. G. ; Ghannam , A. ; Islam , I. ; Liang , M. ; Horuk , R. ; Hesselgesser , J. ; Snider , R. M. ; Perez , H. D. ; Morrissey , M. M. Discovery of novel non-peptide CCR1 receptor antagonists. J. Med. Chem. 1999, 22, 4680–4694.
   Google Scholar
• Hammond , M. L. ; Zambias , R. A. ; Chang , M. N. ; Jensen , N. P. ; McDonald , J. ; Thompson , K. ; Boulton , D. A. ; Kopka , I. E. ; Hand , K. M. ; Opas , E. E. ; Luell , S. ; Bach , T. ; Davies , P. ; MacIntyre , D. E. ; Bonney , R. J. ; Humes , J. L. Antioxidant-based inhibitors of leukotriene biosynthesis: The discovery of 6-[1-[2-(hydroxymethyl)phenyl]-1-propen-3-yl]-2,3-dihydro-5-benzofuranol, a potent topical anti-inflammatory agent . J. Med. Chem. 1990 , 33 , 908 – 919 .
   PubMedGoogle Scholar
• Lulinski , S. ; Zajac , K. Selective generation of lithiated benzonitriles: The importance of reaction conditions . J. Org. Chem. 2008 , 73 , 7785 – 7788 .
   PubMedGoogle Scholar