Synlett 2014; 25(5): 696-700
DOI: 10.1055/s-0033-1340629
letter
© Georg Thieme Verlag Stuttgart · New York

Highly Regioselective Diels–Alder Reaction of 9-Substituted Anthracenes with Citraconic Anhydride

Ruhima Khan
Department of Chemistry, Manipur University, Canchipur 795 003, Manipur, India   Fax: +91(385)2435145   Email: moirangthemds@yahoo.co.in
,
Thokchom Prasanta Singh
Department of Chemistry, Manipur University, Canchipur 795 003, Manipur, India   Fax: +91(385)2435145   Email: moirangthemds@yahoo.co.in
,
Moirangthem Dhaneshwar Singh*
Department of Chemistry, Manipur University, Canchipur 795 003, Manipur, India   Fax: +91(385)2435145   Email: moirangthemds@yahoo.co.in
› Author Affiliations
Further Information

Publication History

Received: 25 November 2013

Accepted after revision: 19 December 2013

Publication Date:
14 January 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.

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