NIS-Mediated Oxidative Lactonization of 2-Arylbenzoic Acids for the Synthesis­ of Dibenzopyranones under Metal-Free Conditions

Abstract

A series of dibenzopyranones were synthesized from 2-arylbenzoic acids by a radical oxidative cyclization procedure mediated by N-iodosuccinimide (NIS). The methodology is distinguished by its practicality in terms of its wide substrate scope, good functional group tolerance, and mild reaction conditions without the use of transition metals.

Key words

lactones - oxidation - carboxylic acids - cyclization - radical reaction

• References

• 1a Bringmann G, Menche D. Acc. Chem. Res. 2001; 34: 615
• 1b Hertweck C, Luzhetskyy A, Rebets Y, Bechthold A. Nat. Prod. Rep. 2007; 24: 162
• 1c Bringmann G, Gulder T, Gulder TA. M, Breuning M. Chem. Rev. 2011; 111: 563
• 1d Zhang Y.-J, Abe T, Tanaka T, Yang C.-R, Kouno I. J. Nat. Prod. 2001; 64: 1527
• 1e Pfundstein B, El Desouky SK, Hull WE, Haubner R, Erben G, Owen RW. Phytochemistry 2010; 71: 1132
• 1f Shepherd MD, Kharel MK, Zhu LL, van Lanen SG, Rohr J. Org. Biomol. Chem. 2010; 8: 3851
• 2a Kemperman GJ, Horst BT, de Goor DV, Roeters T, Bergwerff J, der Eem RV, Basten J. Eur. J. Org. Chem. 2006; 3169
• 2b Hager A, Mazunin D, Mayer P, Trauner D. Org. Lett. 2011; 13: 1386
• 2c Carlson EJ, Riel AM. S, Dahl BJ. Tetrahedron Lett. 2012; 53: 6245
• 3a Renz M, Meunier B. Eur. J. Org. Chem. 1999; 737
• 3b Mehta G, Pandey PN. Synthesis 1975; 404
• 4a Thasana N, Worayuthakarn R, Kradanrat P, Hohn E, Young L, Ruchirawat S. J. Org. Chem. 2007; 72: 9379
• 4b Ceylan S, Klande T, Vogt C, Friese C, Kirschning A. Synlett 2010; 2009
• 5a Harayama T, Yasuda H. Heterocycles 1997; 46: 61
• 6a Inamoto K, Kadokawa J, Kondo Y. Org. Lett. 2013; 15: 3962
• 6b Luo S, Luo F.-X, Zhang X.-S, Shi Z.-J. Angew. Chem. Int. Ed. 2013; 52: 10598
• 7a Li Y, Ding Y.-J, Wang J.-Y, Su Y.-M, Wang X.-S. Org. Lett. 2013; 15: 2574
• 7b Donaire JG, Martin R. J. Am. Chem. Soc. 2013; 135: 9350
• 8a Togo H, Muraki T, Yokoyama M. Tetrahedron Lett. 1995; 36: 7089
• 8b Togo H, Muraki T, Hoshina Y, Yamaguchi K. J. Chem. Soc., Perkin Trans. 1 1997; 787
• 8c Muraki T, Togo H, Yokoyama M. J. Chem. Soc., Perkin Trans. 1 1999; 1713
• 8d Furuyama S, Togo H. Synlett 2010; 2325
• 9a Gao P, Liu J.-J, Wei Y.-Y. Org. Lett. 2013; 15: 2872
• 9b Gao P, Wei Y.-Y. Heterocycl. Commun. 2013; 19: 113
• 9c Gao P, Wei Y.-Y. J. Chem. Res. 2013; 506
• 9d Zhu C.-J, Wei Y.-Y. ChemSusChem 2011; 4: 1082
• 9e Liu H.-X, Wei Y.-Y. Tetrahedron Lett. 2013; 54: 7089
• 10a Beebe TR, Howard FM. J. Am. Chem. Soc. 1969; 91: 3379
• 10b McDonald C, Holcomb H, Kennedy K, Kirkpatrick E, Leathers T, Vanemon P. J. Org. Chem. 1989; 54: 1213
• 10c Kolvari E, Choghamarani AG, Salehi P, Shirini F, Zolfigol MA. J. Iran. Chem. Soc. 2007; 4: 126