Unexpected Truce–Smiles type rearrangement of 2-(2′-pyridyloxy) phenylacetic esters: synthesis of 3-pyridyl-2-benzofuranones
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Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference7 articles.
1. (a) Clough, J. M. Nat. Prod. Rep. 1993, 10, 565. (b) Beautement, K.; Clough, J. M.; de Fraine, P. J.; Godfrey, C. R. A. Pestic. Sci. 1991, 31, 499.
2. (a) Rossi, R.; Bellina, F.; Carpita, A. Synlett 1996, 356. (b) Hodgson, D. M.; Witherington, J.; Moloney, B. A.; Richards, I. C.; Brayer, J.-L. Synlett 1995, 32. (c) Tanimoto, S.; Kokubo, T.; Oida, T.; Ikehira, H. Synth. Commun. 1982, 723.
3. (a) Wittman, M. D.; Kallmerten, J. J. Org. Chem. 1987, 52, 4303. (b) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 2, 5397. (c) Nakata, T.; Kuwabara, T.; Tani, Y.; Oishi, T. Tetrahedron Lett. 1982, 23, 1015.
4. Lithium salts of 2 do not appear to undergo this rearrangement.
5. For similar observations in 3-phenyl-2-benzofuranones, see: (a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425. (b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Chem. Soc., Chem. Commun. 1986,1524.
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