PDF icon Download PDF
Synthesis 2009(10): 1673-1682  
DOI: 10.1055/s-0028-1088058
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

2-(Azidomethyl)arylboronic Acids in the Synthesis of Coumarin-Type Compounds

Mikael I. Naumova, Alexander V. Nucheva, Nikolay S. Sitnikova, Yulia B. Malyshevaa, Andrew S. Shavyrinb, Irina P. Beletskayac, Andrei E. Gavryushind, Sebastien Combese, Alexey Yu. Fedorov*a
a Department of Organic Chemistry, Nizhnii Novgorod N. I. Lobachevsky State University, 23 Gagarin Avenue, 603950 Nizhnii Novgorod, Russian Federation
Fax: +7(831)4658592; e-Mail: afnn@rambler.ru;
b G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Tropinina Street 49, 603600 Nizhnii Novgorod, Russian Federation
e-Mail: andrew@imoc.sinn.ru;
c Department of Chemistry, M.V. Lomonosov State University, Leninskie Gori, 119992 Moscow, Russian Federation
e-Mail: beletska@org.chem.msu.ru;
d Department Chemie and Biochemie, Ludwig Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany
e-Mail: gavch@cup.uni-muenchen.de;
e UMR 6264, Faculte des Sciences Saint-Jerome, Universite d’Aix Marseille 1 et 2, 13397 Marseille Cedex 20, France
e-Mail: Sebastien.Combes@univ-provence.fr;
Further Information

Publication History

Received 9 December 2008
Publication Date:
20 April 2009 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

Several 2-(azidomethyl)arylboronic acids were synthesized. Their involvement into organolead-mediated Pinhey arylation reaction with 4-hydroxycoumarins afforded 3-[2-(azidomethyl)aryl]-4-hydroxycoumarins or [4,3-c]isoquinolino­coumarins in reasonable yields via two- or four-step one-pot reaction sequence. Palladium-catalyzed cross-coupling of organoboron reagents with 4-trifluoromethylsulfonyloxycoumarins under Suzuki reaction conditions gave 4-[2-(azidomethyl)aryl]coumarins in good yields. 2-(Azidomethyl)arylboronic acid, as well as azide-containing iso- and neoflavonoid compounds underwent catalytic alkyne-azide cycloaddition in THF-water, providing 1,4-triazole compounds regioselectively in good to excellent yields.

Key words

coumarins - azides - arylation - cross-coupling - cyclo­addition

    References

  • 1a Donnelly DMX. Boland G. In The Flavonoids: Advances in Research since 1986   Horborne JB. Chapman and Hall; London: 1994.  p.239-258  
  • 1b Barton DHD. Donnelly DMX. Finet J.-P. Guiry PG. J. Chem. Soc., Perkin Trans. 1  1992,  1365 
  • 1c Combes S. Finet J.-P. Siri D. J. Chem. Soc., Perkin Trans. 1  2002,  38 
  • 2a Petit GR. Singh SB. Hamel E. Lin CM. Alberts DS. Garcia-Kendall D. Experientia  1989,  45:  209 
    Search in Google Scholar
  • 2b Petit GR. Singh SB. Boyd MR. Hamel E. Petit RK. Schmidt JM. Hogan FJ. J. Med. Chem.  1995,  38:  1666 
    Search in Google Scholar
  • 2c Nam N.-H. Curr. Med. Chem.  2003,  10:  1697 
    Search in Google Scholar
  • 2d Tron GC. Pirali T. Sorba G. Pagliai F. Busacca S. Genazzani A. J. Med. Chem.  2006,  49:  3033 
    Search in Google Scholar
  • 2e Chaudhary A. Pandeya SN. Kumar P. Sharma PP. Gupta S. Soni N. Verma KK. Bhardwaj G. Mini Rev. Med. Chem.  2007,  7:  1186 
    Search in Google Scholar
  • 3 Taechowisan T. Lu C. Chen Y. Lumyong S. J. Cancer Res. Ther.  2007,  3:  86 
    CrossrefSearch in Google Scholar
  • 4a Bailly C. Bal C. Barbier P. Combes S. Finet J.-P. Hildebrand M.-P. Peyrot V. Wattez N. J. Med. Chem.  2003,  46:  5437 
    Search in Google Scholar
  • 4b Rappl C. Barbier P. Bourgarel-Rey V. Gregoire C. Gilli R. Carre M. Combes S. Finet J.-P. Peyrot V. Biochem.  2006,  45:  9210 
    Search in Google Scholar
  • 5a Oldfield MF. Chen L. Botting NP. Tetrahedron  2004,  60:  1887 
    Search in Google Scholar
  • 5b Dixon RA. Ferreira D. Phytochemistry  2002,  16:  205 
    Search in Google Scholar
  • 6a Adlercreutz H. Lancet Oncol.  2002,  3:  364 
    Search in Google Scholar
  • 6b Morrisey C. Watson RWG. Curr. Drug Targets  2003,  4:  231 
    Search in Google Scholar
  • 7 Anthony MS. Arterioscler. Thromb. Vasc. Biol.  2002,  22:  1245 
    CrossrefSearch in Google Scholar
  • 8 Stark A. Madar Z. J. Pediatr. Endocrinol. Metab.  2002,  15:  561 
    Search in Google Scholar
  • 9 Yamaguchi M. Health Sci.  2002,  48:  209 
    Search in Google Scholar
  • 10a Soleas GJ. Diamandis EP. Goldberg DM. Clin. Biochem.  1997,  30:  91 
    Search in Google Scholar
  • 10b Burns J. Yokota T. Ashihara H. Lean MEJ. Crozier A. J. Agric. Food Chem.  2002,  50:  3337 
    Search in Google Scholar
  • 10c Roberti M. Pizzirani D. Simoni D. Rondanin R. Baruchello R. Bonora C. Buscemi F. Grimaudo S. Tolomeo M. J. Med. Chem.  2003,  46:  3546 
    Search in Google Scholar
  • 11 Pace-Asciak CR. Hahn S. Diamandis EP. Soleas G. Goldberg DM. Clin. Chem. Acta  1995,  235:  207 
    CrossrefSearch in Google Scholar
  • 12 Jang M. Cai L. Udeani GO. Slowing KV. Thomas CF. Beecher CWW. Fong HHS. Farnworth RN. Kinghorn AD. Metha RG. Moon RC. Pezzuto JM. Science  1997,  275:  218 
    CrossrefPubMedSearch in Google Scholar
  • 13a Cushman M. Nagaratham D. Gopal D. Chakraborti AK. Lin CM. Hamel E. J. Med. Chem.  1991,  34:  2579 
    Search in Google Scholar
  • 13b Ohsumi K. Hatanaka T. Fujita K. Nakagawa R. Fukuda Y. Nihei Y. Suga Y. Morinaga Y. Akiyama Y. Tsuji T. Bioorg. Med. Chem. Lett.  1998,  8:  3153 
    Search in Google Scholar
  • 14a Lewis RJ. Sax’s Dangerous Properties of Industrial Materials   Van Nostrand Reinhold; New York: 1992. 
  • 14b Lenga RE. The Sigma-Aldrich Library of Chemical Safety   Sigma-Aldrich; Milwaukee: 1988. 
  • 15a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Search in Google Scholar
  • 15b Suzuki A. J. Organomet. Chem.  1999,  576:  147 
    Search in Google Scholar
  • 15c Llord-Williams P. Giralt E. Chem. Soc. Rev.  2001,  30:  145 
    Search in Google Scholar
  • 15d Hassan J. Sevignon M. Gozzi C. Schulz E. Lamaire M. Chem. Rev.  2002,  102:  1359 
    Search in Google Scholar
  • 16 Morgan J. Pinhey JT. J. Chem. Soc., Perkin Trans. 1  1990,  715 
    Crossref
  • 17 Finet J.-P. Ligand Coupling Reactions with Heteroatomic Compounds   Pergamon Press; Oxford: 1998. 
  • 18a Pinhey JT. In Comprehensive Organometallic Chemistry II   Vol. 11:  Abel EV. Stone FGA. Wilkinson G. Pergamon Press; Oxford: 1995.  Chap. 11.11. p.461-485  
    Search in Google Scholar
  • 18b Finet J.-P. In Comprehensive Organometallic Chemistry III   Vol. 9:  Crabtree RH. Mingos DMP. Elsevier; Oxford: 2006.  Chap. 9.9. p.381-424  
    Search in Google Scholar
  • 18c Elliot CI. Konopelski JP. Tetrahedron  2001,  57:  5683 
    Search in Google Scholar
  • 18d Kano T. Saito S. In Main Group Metals in Organic Synthesis I   Vol. 2:  Yamamoto H. Oshima K. Wiley-VCH; Weinheim: 2004.  p.721-751  
    Search in Google Scholar
  • 19a Culkin DA. Hartwig JF. Acc. Chem. Res.  2003,  36:  234 
    Search in Google Scholar
  • 19b Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1290 
    Search in Google Scholar
  • 19c Miura M. Nomura M. Top. Curr. Chem.  2002,  219:  211 
    Search in Google Scholar
  • 19d Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
    Search in Google Scholar
  • 19e Kakiuchi F. Kochi T. Synthesis  2008,  3013 
  • 20a Barton DHR. Donnelly DMX. Finet J.-P. Guiry PJ. Tetrahedron Lett.  1990,  31:  7449 
    Search in Google Scholar
  • 20b Donnelly DMX. Molloy DJ. Reilly JP. Finet J.-P. J. Chem. Soc., Perkin Trans. 1  1995,  2531 
  • 20c Suginome H. Orito K. Yorita K. Ishikawa M. Shimoyama N. Sasaki T. J. Org. Chem.  1995,  60:  3052 
    Search in Google Scholar
  • 20d Orito K. Sasaki T. Suginome H. J. Org. Chem.  1995,  60:  6208 
    Search in Google Scholar
  • 20e Konopelsky JP. Hottenroth JM. Oltra HM. Veliz EA. Yang Z.-C. Synlett  1996,  609 
  • 20f Naumov MI. Sutirin SA. Shavirin AS. Ganina OG. Bourgarel-Rey V. Beletskaya IP. Finet J.-P. Fedorov AYu. J. Org. Chem.  2007,  72:  3293 
    Search in Google Scholar
  • 21 Sviridov SI. Vasil’ev AA. Sergovskaya NL. Chirskaya MV. Shorshnev SV. Tetrahedron  2006,  62:  2639 
    CrossrefSearch in Google Scholar
  • 22 Brown BR. The Organic Chemistry of Aliphatic Nitrogen Compounds   Clarendon; Oxford: 1994.  p.644-667  
  • 23a Knochel P. Dohle W. Gommermann N. Kneisel FF. Kopp F. Korn T. Sapountzis I. Vu VA. Angew. Chem. Int. Ed.  2003,  42:  4302 
    Search in Google Scholar
  • 23b Knochel P. Krasovskiy A. Sapountzis I. In Handbook of Functionalized Organometallics   Vol. 1:  Knochel P. Wiley-VCH; Weinheim: 2005.  p.109-172  
    Search in Google Scholar
  • 23c Krasovskiy A. Knochel P. Angew. Chem. Int. Ed.  2004,  43:  3333 
    Search in Google Scholar
  • 23d Krasovskiy A. Malakhov V. Gavryushin A. Knochel P. Angew. Chem. Int. Ed.  2006,  45:  6040 
    Search in Google Scholar
  • 24 Wang X.-J. Sun X. Zhang L. Xu Y. Krishnamurthy D. Senanayake CH. Org. Lett.  2006,  8:  305 
    CrossrefSearch in Google Scholar
  • 25a Fedorov AYu. Carrara F. Finet J.-P. Tetrahedron Lett.  2001,  42:  5875 
    Search in Google Scholar
  • 25b Bolshakov AV. Ganina OG. Shavirin AS. Kurski YuA. Finet J.-P. Fedorov AYu. Tetrahedron Lett.  2002,  43:  8245 
    Search in Google Scholar
  • 26 Naumov MI. Ganina OG. Shavirin AS. Beletskaya IP. Finet J.-P. Fedorov AYu. Synthesis  2005,  1178 
    Thieme Connect
  • 27 Fedorov AYu. Shchepalov AA. Bol’shakov AV. Shavyrin AS. Kurskii YuA. Finet J.-P. Zelentsov SV. Russ. Chem. Bull. Int. Ed.  2004,  53:  370 
    CrossrefSearch in Google Scholar
  • 28 Oae S. Croat. Chem. Acta  1986,  59:  129 
    Search in Google Scholar
  • 29 Suzuki H. Matano Y. Organobismuth Chemistry   Elsevier; Amsterdam: 2001. 
  • 30 Grushin VV. Chem. Soc. Rev.  2000,  29:  315 
    CrossrefSearch in Google Scholar
  • 31 Fedorov AYu. Finet J.-P. Eur. J. Org. Chem.  2004,  2040 
    Crossref
  • 32 Scriven EFV. Turnbull K. Chem. Rev.  1988,  88:  297 
    CrossrefSearch in Google Scholar
  • 33a Foch I. Parkanyi L. Besenyei G. Simandi LI. Kalman A. J. Chem. Soc., Dalton Trans.  1999,  293 
  • 33b Nakamura I. Yamamoto Y. Chem. Rev.  2004,  104:  2127 
    Search in Google Scholar
  • 34a Beletskaya IP. Ganina OG. Tsvetkov AV. Fedorov AYu. Finet J.-P. Synlett  2004,  2797 
  • 34b Ganina OG. Daras E. Bourgarel-Rey V. Peyrot V. Andresyuk AN. Finet J.-P. Fedorov AYu. Beletskaya IP. Combes S. Bioorg. Med. Chem.  2008,  16:  8806 
    Search in Google Scholar
  • 35 Tornøe CW. Christensen C. Mendal M. J. Org. Chem.  2002,  67:  3057 
    CrossrefPubMedSearch in Google Scholar
  • 36 Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 
    Search in Google Scholar
  • 37a Bock VD. Hiemstra H. van Maarseveen JH. Eur. J. Org. Chem.  2006,  51 
  • 37b Wu P. Fokin VV. Aldrichimica Acta  2007,  40:  7 
    Search in Google Scholar
  • 39a Boland GM. Donnelly DMX. Finet J.-P. Rea MD. J. Chem. Soc., Perkin Trans. 1  1996,  2591 
  • 39b Donnelly DMX. Finet J.-P. Guiry PJ. Rea MD. Synth. Commun.  1999,  29:  2719 
    Search in Google Scholar
38

Boronic acids 21a-c, like their precursors 4a,b coexist with anhydride forms of boronic acids with different degree of oligomerization. The NMR spectra of 21a-c derivatives purified by crystallization were rather complicated. On the other hand, when compounds 21a-c were isolated by column chromatography on silica gel, the NMR spectra of these products became almost fine due to the cleavage of the ether bonds in the associates.