RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2014; 25(5): 696-700
DOI: 10.1055/s-0033-1340629
DOI: 10.1055/s-0033-1340629
letter
Highly Regioselective Diels–Alder Reaction of 9-Substituted Anthracenes with Citraconic Anhydride
Weitere Informationen
Publikationsverlauf
Received: 25. November 2013
Accepted after revision: 19. Dezember 2013
Publikationsdatum:
14. Januar 2014 (online)
Abstract
The regioselectivity in the Diels–Alder reaction of 9-substituted anthracenes having electron-releasing substituents with citraconic anhydride has been investigated. The ortho regioisomer is preferred in all the cases with good yield. The reaction proceeded best under conventional heating conditions in toluene.
Key words
Diels–Alder reaction - regioselective - diastereoselectivity - cycloaddition - solvent effectsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Diels O, Alder K. Justus Liebigs Ann. Chem. 1926; 237
- 2a Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed. 1998; 37: 388
- 2b Brocksom TJ, Nakamura J, Ferreira ML, Brocksom U. J. Braz. Chem. Soc. 2001; 12: 597
- 3 Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
- 4a Williams RM, Stocking EM. Angew. Chem. Int. Ed. 2003; 42: 3078
- 4b Martin J, David T. Chem. Soc. Rev. 2009; 38: 2983
- 5 Kazutaka S, Kentaro F, Fumito K, Seiji I, Hisashi Y. J. Am. Chem. Soc. 2010; 132: 5625
- 6a Futatsugi K, Yamamoto H. Angew. Chem. Int. Ed. 2005; 44: 1484
- 6b Liu D, Canales E, Corey EJ. J. Am. Chem. Soc. 2007; 129: 1498
- 7 Corey EJ. Angew. Chem. Int. Ed. 2002; 41: 1650
- 8 Mehta G, Uma R. Acc. Chem. Res. 2000; 33: 278
- 9 Kanishchev OS, Sanselme M, Bouillon JP. Tetrahedron 2013; 69: 1322
- 10 Liu X, Snyder JK. J. Org. Chem. 2008; 73: 2935
- 11 Burgess KL, Corbett MS, Eugenio P, Lajkiewicz NJ, Liu X, Sanyal A, Yan W, Yuan Q, Snyder JK. Bioorg. Med. Chem. 2005; 13: 5299
- 12 Sanyal A, Yuan Q, Snyder JK. Tetrahedron Lett. 2005; 46: 2475
- 13 Burgess KL, Lajkiewicz NJ, Sanyal A, Yan W, Snyder JK. Org. Lett. 2005; 7: 31
- 14 Corbett MS, Liu X, Sanyal A, Snyder JK. Tetrahedron Lett. 2003; 44: 931
- 15 Jones S, Valette D. Org. Lett. 2009; 11: 5358
- 16a Adams H, Jones S, Ojea-Jimenez I. Org. Biomol. Chem. 2006; 4: 2296
- 16b Adams H, Bawa AR, Jones S. Org. Biomol. Chem. 2006; 4: 4206
- 17 Sanyal A, Snyder JK. Org. Lett. 2000; 2: 2527
- 18 Alston PV, Ottenbrite RM, Newby J. J. Org. Chem. 1979; 44: 4939
- 19 Yang BV, Doweyko LM. Tetrahedron Lett. 2005; 46: 2857
- 20 Verma SM, Singh MD. J. Org. Chem. 1977; 42: 3736
- 21 Singh MD, Jay S, Silvio EB, Kurt M. J. Am. Chem. Soc. 1987; 109: 3397
- 22 Singh MD, Anjana N. Indian. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2010; 49: 789
- 23 Singh MD, Anjana N. Indian J. Chem. Sect. B, Org. Chem. Incl. Med. Chem. 2010; 49: 77
- 24 Xie F, Sivakumar K, Zeng Q, Bruckman MA, Hodges B, Wand Q. Tetrahedron 2008; 64: 2906
- 25 Zimmermman C, Mohr M, Zipse H, Eichberger R, Schnabel W. J. Photochem. Photobiol. A. 1999; 125: 47
- 26 Lan P, Berta D, Porco JA. Jr, South MS, Parlow JJ. J. Org. Chem. 2003; 68: 9678
- 27 Ariel MS, Madeleine MJ, Rolando AS, Alejandra GS. Org. Lett. 2006; 8: 5561