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Synthesis 2012; 44(21): 3392-3398
DOI: 10.1055/s-0032-1316777
paper
© Georg Thieme Verlag Stuttgart · New York

Functionalization of Chromones through an Aza-Baylis–Hillman-Type Reaction

Michael A. Terzidis
a   Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Macedonia, Greece
,
Vassilios G. Tsiaras
a   Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Macedonia, Greece
,
Julia Stephanidou-Stephanatou*
a   Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Macedonia, Greece
,
Constantinos A. Tsoleridis*
a   Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Macedonia, Greece
,
Vassilis Psycharis
b   Institute of Materials Science, NCSR Demokritos, 15310 Aghia Paraskevi Attikis, Greece   Fax: +30(2310)997679   eMail: ioulia@chem.auth.gr   eMail: tsolerid@chem.auth.gr
,
Catherine P. Raptopoulou
b   Institute of Materials Science, NCSR Demokritos, 15310 Aghia Paraskevi Attikis, Greece   Fax: +30(2310)997679   eMail: ioulia@chem.auth.gr   eMail: tsolerid@chem.auth.gr
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Publikationsverlauf

Received: 17. Juli 2012

Accepted after revision: 22. August 2012

Publikationsdatum:
17. September 2012 (online)

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Abstract

The synthesis of (N,N′-bisalkoxycarbonyl)hydrazinochromones via the aza-Baylis–Hillman reaction of formylchromones and azodicarboxylates is reported. A plausible mechanistic scheme for the formation of these compounds, involving the chromone formyl group elimination, is proposed. Conformational analysis was performed by DFT calculations. The structure of one example was confirmed by XRD investigation. Full assignment of all 1H and 13C NMR chemical shifts has been unambiguously achieved.

Key words

azodicarboxylates - formylchromones - DABCO - aza-Baylis–Hillman reaction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

    • 1a Yang Y, Xu Y, Xia T, Chen F, Zhang C, Liang W, Lai L, Fang X. Chem. Commun. 2011; 47: 5440
      CrossrefSuche in Google Scholar
    • 1b Hyz K, Kawecki R, Misior A, Bocian W, Bednarek E, Sitkowski J, Kozerski L. J. Med. Chem. 2011; 54: 8386
      CrossrefSuche in Google Scholar
    • 1c Gobbi S, Cavalli A, Rampa A, Belluti F, Piazzi L, Paluszcak A, Hartmann RW, Recanatini M, Bisi A. J. Med. Chem. 2006; 49: 4777
      CrossrefPubMedSuche in Google Scholar
    • 1d Nutley BP, Smith NF, Hayes A, Kelland LR, Brunton L, Golding BT, Smith GC. M, Martin NM. B, Workman P, Raynaud FI. Br. J. Cancer 2005; 93: 1011
      Suche in Google Scholar
    • 1e Boumendjel A, Nicolle E, Moraux T, Gerby B, Blanc M, Ronot X, Boutonnat J. J. Med. Chem. 2005; 48: 7275
      CrossrefSuche in Google Scholar
    • 1f Ahmed-Belkacem A, Pozza A, Muñoz-Martínez F, Bates SE, Castanys S, Gamarro F, Di Pietro A, Pérez-Victoria JM. Cancer Res. 2005; 65: 4852
      CrossrefSuche in Google Scholar
    • 1g Morris J, Wishka DG, Lin AH, Humphrey WR, Wiltse AL, Gammill RB, Judge TM, Bisaha SN, Olds NL, Jacob CS, Bergh CL, Cudahy MM, Williams DJ, Nishizawa EE, Thomas EW, Gorman RR, Benjamin CW, Shebuski RJ. J. Med. Chem. 1993; 36: 2026
      CrossrefSuche in Google Scholar
    • 1h Horie T, Tominaga H, Kawamura Y, Hada T, Ueda N, Amano Y, Yamamoto S. J. Med. Chem. 1991; 34: 2169
      CrossrefSuche in Google Scholar
  • 5 Quiney C, Dauzonne D, Kern C, Fourneron J.-D, Izard J.-C, Mohammad RM, Kolb J.-P, Billard C. Leukemia Res. 2004; 28: 851
    CrossrefSuche in Google Scholar
  • 6 Beudot C, De Méo MP, Dauzonne D, Elias R, Laget M, Guiraud H, Balansard G, Duménil G. Mutat. Res. 1998; 417: 141
    CrossrefSuche in Google Scholar
  • 7 Geissler JF, Roesel JL, Meyer T, Trinks UP, Traxler P, Lydon NB. Cancer Res. 1992; 52: 4492
    PubMedSuche in Google Scholar
  • 12 Wu C, Liu Y, Zeng H, Liu L, Wang D, Chen Y. Org. Biomol. Chem. 2011; 9: 253
    CrossrefSuche in Google Scholar
  • 15 Papafilippou A, Terzidis MA, Stephanidou-Stephanatou J, Tsoleridis CA. Tetrahedron Lett. 2011; 52: 1306
    CrossrefSuche in Google Scholar
  • 16 Terzidis MA, Tsoleridis CA, Stephanidou-Stephanatou J, Terzis A, Raptopoulou CP, Psycharis V. Tetrahedron 2008; 64: 11611
    CrossrefSuche in Google Scholar
  • 17 Complete crystallographic data for compound 3a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 882016. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336 033, e-mail: deposit@ccdc.cam.ac.uk
  • 18 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA. Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM. W, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian03, rev. E.01 11-Sep-2007 . Gaussian, Inc; Wallingford CT: 2004
    Suche in Google Scholar