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RESEARCH ARTICLE
Contents Vol 63(11)

Efficient Synthesis of Chromones with Alkenyl Functionalities by the Heck Reaction

Tamás Patonay A C , Attila Vasas A , Attila Kiss‐Szikszai A , Artur M. S. Silva B and José A. S. Cavaleiro B
+ Author Affiliations
- Author Affiliations

A Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, H‐4032 Debrecen, Hungary.

B Department of Chemistry and Química Orgânica, Produtos Naturais e Agroalimentares, University of Aveiro, 3810‐193 Aveiro, Portugal.

C Corresponding author. Email: tpatonay@puma.unideb.hu

Australian Journal of Chemistry 63(11) 1582-1593 https://doi.org/10.1071/CH10295
Submitted: 9 August 2010  Accepted: 7 October 2010   Published: 11 November 2010

Abstract

The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl‐substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine‐free conditions using a phase‐transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.


References

[1]     (a) (a) R. F. Heck, in Comprehensive Organic Synthesis (Eds B. M. Trost, I. Fleming) 1991, Vol. 4, p. 883 (Pergamon: Oxford, UK).
         (b) (b) M. Shibasaki, F. Miyazaki, in Handbook of Organo‐Palladium Chemistry for Organic Synthesis (Ed. E. Negishi) 2002, Vol. 1, p. 1283 (Wiley‐Interscience: New York).
      (c) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) N. J. Whitcombe, K. K. Hii, S. E. Gibson, Tetrahedron 2001, 57, 7449.
         | Crossref | GoogleScholarGoogle Scholar |
         (e) (e) S. Bräse, A. de Meijere, in Metal‐Catalyzed Cross‐Coupling Reactions (Eds A. de Meijere, F. Diederich) 2004, p. 217 (Wiley‐VCH: Weinheim).

[2]  (a) S. G. Davies, B. E. Mobbs, J. Chem. Soc., Perkin Trans. 1 1987, 2597.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXktlOks7w%3D&md5=c2913d03fd94ccd03ad5fd40b88eb1edCAS |
      (b) K. M. Dawood, Tetrahedron 2007, 63, 9642.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) A. S. Klymchenko, Y. Mély, Tetrahedron Lett. 2004, 45, 8391.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXotlSnu7c%3D&md5=83d9149ac9f5d77825cd47ed006b0871CAS |
      (b) A. S. Klymchenko, H. Stoeckel, K. Takeda, Y. Mély, J. Phys. Chem. B 2006, 110, 13624.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) C. M. M. Santos, A. M. S. Silva, J. A. S. Cavaleiro, Synlett 2005, 20, 3095.
      (b) C. M. M. Santos, A. M. S. Silva, J. A. S. Cavaleiro, Synlett 2007, 20, 3113.

[5]  (a) K. Dahlén, M. Grotli, K. Luthman, Synlett 2006, 897.
      (b) K. Dahlén, E. A. A. Wallén, M. Grotli, K. Luthman, J. Org. Chem. 2006, 71, 6863.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  K. Tatsuta, S. Kasai, Y. Amano, T. Yamaguchi, M. Seki, S. Hosokawa, Chem. Lett. 2007, 36, 10.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXpt1CrtQ%3D%3D&md5=51ca93c494d8fe1f116642299da82139CAS |

[7]  R. Sarges, J. Bordner, B. W. Dominy, M. J. Peterson, E. B. Whipple, J. Med. Chem. 1985, 28, 1716.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXls1Sntrw%3D&md5=032e1a5fb17671e7076bfe0e0744973eCAS | 3934383PubMed |

[8]  T. Patonay, J. A. S. Cavaleiro, A. Lévai, A. M. S. Silva, Heterocycl. Commun. 1997, 3, 223.
         | 1:CAS:528:DyaK2sXksFaisLg%3D&md5=1b49781c0aa99f5b0ebf297d2e31e5c9CAS |

[9]  R. B. Gammill, Synthesis 1979, 901.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXhsVKmtr0%3D&md5=7e29d86e9446ee76b9f2aed6715fe9a9CAS |

[10]  J. Chen, Y. Zhang, L. Yang, X. Zhang, J. Liu, L. Li, H. Zhang, Tetrahedron 2007, 63, 4266.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXktF2hs7w%3D&md5=946b2c00cabec888b0e108d43087cc4aCAS |

[11]  G. Battistuzzi, S. Cacchi, G. Fabrizi, Org. Lett. 2003, 5, 777.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtFSgtro%3D&md5=4b30c1af5a2b01e7a01cc0174357ef81CAS | 12605513PubMed |

[12]  (a) T. Jeffery, J. Chem. Soc. Chem. Commun. 1984, 1287.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXhtlWltrc%3D&md5=1798fe94cc24459bebb488d990d27925CAS |
      (b) T. Jeffery, Tetrahedron Lett. 1985, 26, 2667.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) T. Jeffery, Tetrahedron 1996, 52, 10113.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  A. S. Kelkar, R. M. Letcher, K.‐K. Cheung, K.‐F. Chiu, G. D. Brown, J. Chem. Soc., Perkin Trans. 1 2000, 3732.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXnvVylt7s%3D&md5=461a6b4771c8968edd0da2f3a8ab906eCAS |

[14]  A. M. S. Silva, D. C. G. A. Pinto, J. A. S. Cavaleiro, A. Lévai, T. Patonay, Arkivoc 2004, vii, 106.

[15]  C. K. Ghosh, S. Bhattacharyya, C. Ghosh, A. Patra, J. Chem. Soc., Perkin Trans. 1 1999, 3005.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXms12qtb8%3D&md5=c91babb6e08b753f4215e7831de115f1CAS |

[16]  (a) D. C. G. A. Pinto, A. M. S. Silva, J. R. Carrillo, A. Díaz‐Ortiz, A. de la Hoz, J. A. S. Cavaleiro, Synlett 2003, 1415.
         | 1:CAS:528:DC%2BD3sXmsFOmsbo%3D&md5=b6b385a5ffe4a978593c03efff60c116CAS |
      (b) D. C. G. A. Pinto, A. M. S. Silva, C. M. Brito, A. Sandulache, J. R. Carrillo, A. Díaz‐Ortiz, A. de la Hoz, J. A. S. Cavaleiro, Eur. J. Org. Chem. 2005, 2973.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  J. Heredia‐Moya, K. Krohn, U. Flörke, H. Pessoa‐Mahana, B. Weiss‐López, A. Estévez‐Braun, R. Araya‐Maturana, Heterocycles 2007, 71, 1327.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmsV2ntbw%3D&md5=96801eb55e25ce63f457b9a6f5a8f5a4CAS |

[18]  V. E. Kataev, Zh. Obsch. Khim 1988, 58, 1348.
         | 1:CAS:528:DyaL1MXls1Oksw%3D%3D&md5=be8253fec1f5da0feb94c37412d51abbCAS |

[19]  R. H. Hall, J. Chem. Soc. 1949, 2035.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3cXnsV2r&md5=86cc912dcf254a9e1cff45d21a3253b6CAS |

[20]  G. Canalini, Ann. Chim. 1967, 57, 1045.
         | 1:CAS:528:DyaF1cXktVaku7Y%3D&md5=62820ffddb59236617a4abf0f5548338CAS |

[21]  P. F. Wiley, J. Am. Chem. Soc. 1951, 73, 4205.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG38XhslKjtQ%3D%3D&md5=6c0a68b2bb2e9ce928545f02c321503fCAS |

[22]  G. P. Ellis, I. L. Thomas, J. Chem. Soc., Perkin Trans. 1 1973, 2781.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXntVKmsg%3D%3D&md5=511a258a0f87d1d05282e6d3ae5fbd47CAS |

[23]  M. Ferrali, D. Donati, S. Bambagioni, M. Fontani, G. Giorgi, A. Pietrangelo, Bioorg. Med. Chem. 2001, 9, 3041.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXosVGku70%3D&md5=eed662ee6c61421e4f841b65df78f1f3CAS | 11597487PubMed |

[24]  A. Nishinaga, H. Ando, K. Marayama, T. Mashino, Synthesis 1992, 839.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38Xmtleku7w%3D&md5=36067fc35b259fd488df9a3cc7bdcdf4CAS |

[25]  I. Hirao, M. Yamaguchi, M. Hamada, Synthesis 1984, 1076.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXktlOgsLY%3D&md5=5e1a3ae5283e4ace73d0e43ea1447149CAS |

[26]  C. W. Winter, C. S. Hamilton, J. Am. Chem. Soc. 1952, 74, 3999.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3sXisFektw%3D%3D&md5=4c1c6073467408c16fec4205fb0c6ca6CAS |

[27]  M. Yamauchi, S. Katayama, Y. Nakashita, T. Watanabe, Synthesis 1981, 33.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  C. M. M. Santos, A. M. S. Silva, J. A. S. Cavaleiro, Eur. J. Org. Chem. 2009, 2642.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmtVCisL8%3D&md5=3cc2d8948f36b8cad63e9f8885a30e7cCAS |

[29]  A.‐T. Dang, D. O. Miller, L. N. Dawe, G. J. Bodwell, Org. Lett. 2008, 10, 233.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVCisLjL&md5=d2337d6398463d11d54df187edceabe0CAS | 18092790PubMed |

[30]  G. J. Bodwell, K. M. Hawco, R. P. da Silva, Synlett 2003, 179.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXht12ktbc%3D&md5=48d25fbdc2144ec95b1b2488368fb904CAS |

[31]  F. Silva, M. Reiter, R. Mills‐Webb, M. Sawicki, D. Klär, N. Bensel, A. Wagner, V. Gouverneur, J. Org. Chem. 2006, 71, 8390.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVShs7jE&md5=eb6a4ea9fa371be65cfb48da8083c13bCAS | 17064010PubMed |

[32]  A. Nohara, H. Kuriki, T. Saijo, H. Sugihara, M. Kanno, Y. Sanno, J. Med. Chem. 1977, 20, 141.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2sXhtFCqtbs%3D&md5=0bc73e67f699af8064c7e3cb084c98cdCAS |

[33]  A. P. Shkumat, Zh. Obsch. Khim. 1989, 59, 1116.
         | 1:CAS:528:DyaK3cXlsVGmsw%3D%3D&md5=ac909887bd92d219cbce254e7119eff5CAS |

[34]  R. H. F. Manske, J. Am. Chem. Soc. 1950, 72, 4797.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3MXislSgsw%3D%3D&md5=abfcf6ceaa6cafd2e7d377924770d555CAS |

[35]  http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi [verified 11 October 2010], SDBD No. 1191‐HSP‐41–130, 1191‐CDS‐03–200.