Oxidation of Chromenes with Iodine(III)

Oxidation of Chromenes with Iodine(III)

Ahmad, Anees; Jr., Luiz F. Silva

Abstract:

Hypervalent iodine reagents play a key role for a variety of synthetic transformations. The successful ring contraction of 1,2-dihydronaphthalenes mediated by PhI(OH)OTs (HTIB) in different organic solvents (Scheme 1), was a valuable discovery during the course of our synthetic studies aiming the diastereoselective total synthesis of (±)-indatraline. Based on these results, we decided to expand our area of focus towards ring contraction of chromenes into benzofuranes (Scheme 2), which is an important class of bioactive natural products. Herein, we present a series of reactions with 2H-chromenes and 4-methyl- 2H-chromene using HTIB under different conditions

Hypervalent iodine reagents play a key role for a variety of synthetic transformations. The successful ring contraction of 1,2-dihydronaphthalenes mediated by PhI(OH)OTs (HTIB) in different organic solvents (Scheme 1), was a valuable discovery during the course of our synthetic studies aiming the diastereoselective total synthesis of (±)-indatraline. Based on these results, we decided to expand our area of focus towards ring contraction of chromenes into benzofuranes (Scheme 2), which is an important class of bioactive natural products. Herein, we present a series of reactions with 2H-chromenes and 4-methyl- 2H-chromene using HTIB under different conditions

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DOI: 10.5151/chempro-14bmos-R0212-2

Referências bibliográficas

• [1] 1 Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. 2 Silva, L. F., Jr.; Siqueira, F. A.; Pedrozo, E. C.; Vieira, F. Y. M.
• [2] Doriguetto, A. C. Org. Lett. 2007, 9, 1433. 3 McCallion, G. D. Curr. Org. Lett. 1999,3, 67.

Como citar:

Ahmad, Anees; Jr., Luiz F. Silva; "Oxidation of Chromenes with Iodine(III)", p-212-212. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0212-2