Synthesis of Isocoumarin via PTSA-Catalyzed Annulation of Diarylalkynes

Gaëlle Le Bras; Abdallah Hamze; Samir Messaoudi; Olivier Provot; Pierre-Benoît Le Calvez; Jean-Daniel Brion; Mouâd Alami

doi:10.1055/s-2008-1072575

PAPER

Synthesis of Isocoumarin via PTSA-Catalyzed Annulation of Diarylalkynes

Gaëlle Le Bras, Abdallah Hamze, Samir Messaoudi, Olivier Provot*, Pierre-Benoît Le Calvez, Jean-Daniel Brion, Mouâd Alami*
Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud XI, CNRS, BioCIS, UMR 8076, rue J. B. Clément, 92296 Châtenay-Malabry, France
Fax: +33(1)46835828; e-Mail: olivier.provot@u-psud.fr; e-Mail: mouad.alami@u-psud.fr;

Abstract

All articles of this category

Abstract

p-Toluenesulfonic acid (PTSA) in ethanol was used as a mild acid catalyst for the annulation of various functionalized diarylalkynes under microwave irradiation. This metal-free process allowed the synthesis of a range of 3-aryl-substituted isocoumarins in good yields.

Key words

alkynes - annulations - isocoumarin - isochromene - microwave activation

Full Text

References

1 Matsuda H. Shimoda H. Yoshikawa M. Bioorg. Med. Chem. 1999, 7: 1445

2 Yoshikawa M. Harada E. Naitoh Y. Inoue K. Matsuda H. Shimoda H. Yamahara J. Murakami N. Chem. Pharm. Bull. 1994, 42: 2225

3 Nozawa K. Yamada M. Tsuda Y. Kawai K. Nakajima S. Chem. Pharm. Bull. 1981, 29: 2689

4 Furuta T. Fukuyama Y. Asakawa Y. Phytochemistry 1986, 25: 517

5 Matsuda H. Shimoda H. Yamahara J. Yoshikawa M. Bioorg. Med. Chem. Lett. 1998, 8: 215

6 Whyte AC. Gloer JB. Scott JA. Mallock D. J. Nat. Prod. 1996, 59: 765

7 Lee JH. Park YJ. Kim HS. Hong YS. Kim K.-W. Lee JJ. J. Antibiot. 2001, 54: 463

8 For a review, see: Napolitano E. Org. Prep. Proced. Int. 1997, 29: 631

For some recent examples, see:

9a Cherry K. Parrain J.-L. Thibonnet J. Duchêne A. Abarbri M. J. Org. Chem. 2005, 70: 6669

9b Woon EC. Dhami A. Mahon MF. Threadgill MD. Tetrahedron 2006, 62: 4829

9c Uchiyama M. Ozawa H. Takuma K. Matsumoto Y. Yonehara M. Hiroya K. Sakamoto T. Org. Lett. 2006, 8: 5517

9d Marchal E. Uriac P. Legouin B. Toupet L. van de Weghe P. Tetrahedron 2007, 63: 9979

10 Hellal M. Bourguignon J.-J. Bihel F. Tetrahedron Lett. 2008, 49: 62

11 Olivi N. Thomas E. Peyrat J.-F. Alami M. Brion J.-D. Synlett 2004, 2175

12 Le Bras G. Provot O. Peyrat J.-F. Alami M. Brion J.-D. Tetrahedron Lett. 2006, 47: 5497

13a Bekaert A. Provot O. Rasolojaona O. Peyrat J.-F. Alami M. Brion J.-D. Tetrahedron Lett. 2005, 46: 4187

13b Le Bras G. Provot O. Bekaert A. Peyrat J.-F. Alami M. Brion J.-D. Synthesis 2006, 1537

13c L’Hermite N. Giraud A. Provot O. Peyrat J.-F. Alami M. Brion J.-D. Tetrahedron 2006, 62: 11994

13d Giraud A. Provot O. Peyrat J.-F. Alami M. Brion J.-D. Tetrahedron 2006, 62: 7667

14a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 4467

14b Alami M. Ferri F. Linstrumelle G. Tetrahedron Lett. 1993, 34: 6403