Organocatalyzed Reactions Involving 3-Formylchromones and Acetylenedicarboxylates: Efficient Synthesis of Functionalized Benzophenones and Polysubstituted Xanthones

Abstract

Organocatalyzed reactions between chromones and acetylenedicarboxylates leading either to xanthone derivatives or to functionalized benzophenones are described. The outcome of the reactions was found to depend both on the nature of the chromone substituents and on the basicity of the organocatalyst.

Key words

DMAP - hetero-Diels-Alder reactions - Friedel-Crafts reactions - organocatalysis - xanthones - zwitterions

References

• For selected reviews, see:
• 1a Barbas CF. Angew. Chem. Int. Ed.  2008,  47:  42 
• 1b List B. Chem. Rev.  2007,  107:  5413 ; thematic issue: Organocatalysis
• 1c In Enantioselective Organocatalysis, Reactions and Experimental Procedures   Dalko PI. Wiley-VCH; Weinheim: 2007. 
• 1d Pellissier H. Tetrahedron  2007,  63:  9267 
• 1e Pellissier H. Tetrahedron  2006,  62:  242 ; thematic issue: Organocatalysis in Organic Synthesis
• 1f List B. Chem. Commun.  2006,  819 
• 1g Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis   Berkessel A. Gröger H. Wiley-VCH; Weinheim: 2005. 
• 1h Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2004,  43:  5138 
• 1i Dalko PI. Moisan L. Adv. Synth. Catal.  2004,  346:  1007 ; thematic issue: Organic Catalysis
• 1j Houk KN. List B. Acc. Chem. Res.  2004,  37:  487 ; thematic issue: Asymmetric Organocatalysis
• 1k Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2001,  40:  3726 
• 2 List B. Lerner RA. Barbas CF. J. Am. Chem. Soc.  2000,  122:  2395 
• 3a Nair V. Sreekanth AR. Vinod AU. Org. Lett.  2001,  3:  3495 
• 3b Li C.-Q. Shi M. Org. Lett.  2003,  5:  4273 
• 3c Nair V. Pillai AN. Menon RS. Suresh E. Org. Lett.  2005,  7:  1189 
• 3d Nair V. Pillai AN. Beneesh PB. Suresh E. Org. Lett.  2005,  7:  4625 
• 3e Pillai AN. Suresh E. Nair V. Chem. Eur. J.  2008,  14:  5851 
• 4 Nair V. Vidya N. Biju AT. Deepthi A. Abhilash KG. Suresh E. Tetrahedron  2006,  62:  10136 
• 5a Waldmann H. Khedkar V. Dückert H. Schürmann M. Oppel IM. Kumar K. Angew. Chem. Int. Ed.  2008,  47:  6869 
• 5b Khedkar V. Liu W. Dückert H. Kumar K. Synlett  2010,  403 
• 6 Terzidis MA. Dimitriadou E. Tsoleridis CA. Stephanidou-Stephanatou J. Tetrahedron Lett.  2009,  50:  2174 
• 7a Liou J.-P. Chang J.-Y. Chang C.-W. Chang C.-Y. Mahindroo N. Kuo F.-M. Hsieh H.-P. J. Med. Chem.  2004,  47:  2897 
• 7b Liou J.-P. Chang C.-W. Song JS. Yang Y.-N. Yeh C.-F. Tseng H.-Y. Lo Y.-K. Chang Y.-L. Chang C.-M. Hsieh H.-P. J. Med. Chem.  2002,  45:  2556 
• 7c Pettit GR. Toki B. Herald DL. Verdier-Pinard P. Boyd MR. Hamel E. Pettit RK. J. Med. Chem.  1998,  41:  1688 
• 8 Buchta E. Egger H. Chem. Ber.  1957,  90:  2760 
• 9 Shiue J.-S. Lin M.-H. Fang J.-M. J. Org. Chem.  1997,  62:  4643 
• 10a Langer P. Appel B. Tetrahedron Lett.  2003,  44:  7921 
• 10b Yawer MA. Hussain I. Fischer C. Görls H. Langer P. Tetrahedron  2008,  64:  894 
• 11a El-Seedi HR. El-Ghorab DMH. El-Barbary MA. Zayed MF. Göransson U. Larsson S. Verpoorte R. Curr. Med. Chem.  2009,  16:  581 
• 11b Nguyen HT. Lallemand M.-C. Boutefnouchet S. Michel S. Tillequin F. J. Nat. Prod.  2009,  72:  527 
• 11c Wu Z. Wei G. Lian G. Yu B. J. Org. Chem.  2010,  75:  5725 
• 12 Pickert M. Frahm AW. Arch. Pharm. Pharm. Med. Chem.  1998,  177 
• 13a Basel Y. Hassner A. J. Org. Chem.  2000,  65:  6368 
• 13b Basel Y. Hassner A. Tetrahedron Lett.  2002,  43:  2529 

14

The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.5, available from: ftp://davinci.chem.umanitoba.ca/pub/marat/SpinWorks/