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

Ruhima Khan; Thokchom Prasanta Singh; Moirangthem Dhaneshwar Singh

doi:10.1055/s-0033-1340629

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(5): 696-700
DOI: 10.1055/s-0033-1340629

letter

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

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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 effects

Volltext

Referenzen

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

Zusatzmaterial

Supporting Information