Synthesis of isocoumarin via PTSA-catalyzed annulation of diarylalkynes

Synthesis

Volumn , Issue 10, 2008, Pages 1607-1611

  Le Bras, Gaëlle ^a   Hamze, Abdallah ^a   Messaoudi, Samir ^a   Provot, Olivier ^a   Le Calvez, Pierre Benoît ^a   Brion, Jean Daniel ^a   Alami, Mouâd ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Alkynes; Annulations; Isochromene; Isocoumarin; Microwave activation

Indexed keywords

ETHANOL; MICROWAVES;

(E ,3E) PROCESS; CATALYZED ANNULATION; DIARYLALKYNES; FUNCTIONALIZED; GOOD YIELDS; ISOCOUMARINS; MILD ACIDS; P TOLUENE SULFONIC ACID (PTSA); SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

MICROWAVE IRRADIATION;

3 (2 METHOXYPHENYL)ISOCOUMARIN; 3 (3,4,5 TRIMETHOXYPHENYL)ISOCOUMARIN; 3 (4 AMINOPHENYL)ISOCOUMARIN; 3 (4 METHOXYPHENYL) 7 NITROISOCOUMARIN; 3 (4 METHOXYPHENYL)ISOCOUMARIN; 3 (4 METHYLPHENYL)ISOCOUMARIN; 3 (NAPHTHALEN 1 YL)ISOCOUMARIN; 3 (PYRIDIN 2 YL)ISOCOUMARIN; 7 METHOXY 3 (4 METHOXYPHENYL)ISOCOUMARIN; ISOCOUMARIN DERIVATIVE; METAL; TOLUENESULFONIC ACID DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; SYNTHESIS;

EID: 44949100255     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072575     Document Type: Article

References (21)

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, A. C.; Gloer, J. B.; Scott, J. A.; Mallock, D. J. Nat. Prod. 1996, 59, 765.
7. Lee, J. H.; Park, Y. J.; Kim, H. S.; Hong, Y. S.; Kim, K.-W.; Lee, J. J. J. Antibiot. 2001, 54, 463.
8. For a review, see: Napolitano, E. Org. Prep. Proced. Int. 1997, 29, 631.
9. For some recent examples, see: (a) Cherry, K.; Parrain, J.-L.; Thibonnet, J.; Duchêne, A.; Abarbri, M. J. Org. Chem. 2005, 70, 6669.
10. (b) Woon, E. C.; Dhami, A.; Mahon, M. F.; Threadgill, M. D. Tetrahedron 2006, 62, 4829.
11. (c) Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517.
12. (d) Marchai, E.; Uriac, P.; Legouin, B.; Toupet, L.; van de Weghe, P. Tetrahedron 2007, 63, 9979.
13. Hellal, M.; Bourguignon, J.-J.; Bihel, F. Tetrahedron Lett. 2008, 49, 62.
14. Olivi, N.; Thomas, E.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Synlett 2004, 2175.
15. Le Bras, G.; Provot, O.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Tetrahedron Lett. 2006, 47, 5497.
16. (a) Bekaert, A.; Provot, O.; Rasolojaona, O.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Tetrahedron Lett. 2005, 46, 4187.
17. (b) Le Bras, G.; Provot, O.; Bekaert, A.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Synthesis 2006, 1537.
18. (c) L'Hermite, N.; Giraud, A.; Provot, O.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Tetrahedron 2006, 62, 11994.
19. (d) Giraud, A.; Provot, O.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Tetrahedron 2006, 62, 7667.
20. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
21. (b) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.