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Synlett 2005(4): 599-602
DOI: 10.1055/s-2005-863717
DOI: 10.1055/s-2005-863717
LETTER
© Georg Thieme Verlag Stuttgart · New YorkCu(I)-Catalyzed Cyclized Coupling Reaction of o-Ethynylphenylphosphonic Acid Monoesters with Allyl Bromide
Weitere Informationen
Received
7 December 2004
Publikationsdatum:
22. Februar 2005 (online)
Publikationsverlauf
Publikationsdatum:
22. Februar 2005 (online)

Abstract
4-Allylphosphaisocoumarins can be prepared in good yield and with high regioselectivity by the reaction of o-ethynylphenylphosphonic acid monoesters with allyl bromide catalyzed by CuI. The present reaction represents the first example of a phosphonic acid monoester cyclized coupling reaction with alkyl halide.
Key words
phosphaisocoumarin - bioactivity - o-ethynylphenylphosphonic acid monoester - cyclization - coupling
- 1a
Powers JC.Asgian JL.Ekici D.James KE. Chem. Rev. 2002, 102: 4639 ; and references therein - 1b
Nozawa K.Yamada M.Tsuda Y.Kawai KI.Nakajima S. Chem. Pharm. Bull. 1981, 29: 2491 - 1c
Hussain MT.Rama NH.Malik A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 372 - 1d
Lee JH.Park YJ.Kim HS.Hong YS.Kim KW.Lee JJ. J. Antibiot. 2001, 54: 463 - 1e
Whyte AC.Gloer JB.Mallock D. J. Nat. Prod. 1996, 59: 765 - 1f
Shimoda H.Matsuda H.Yamahara J.Yoshikawa M. Biol. Pharm. Bull. 1998, 21: 809 - 1g
Umehara K.Matsumoto M.Nakamura M.Miyase T.Kuronagi M.Noguchi H. Chem. Pharm. Bull. 2000, 48: 566 - 2a
Handbook of Organophosphorus Chemistry
Engel R. Marcel Dekker; New York: 1992. Chap. 11. - 2b
A Guide to Organophosphorus Chemistry
Quin LD. John Wiley and Sons; New York: 2000. Chap. 11. - 3
Peng A.-Y.Ding Y.-X. J. Am. Chem. Soc. 2003, 125: 15006 - 4a
Yanagihara N.Lambert C.Iritani K.Utimoto K.Nozaki H. J. Am. Chem. Soc. 1986, 108: 2753 - 4b
Tetsuo T.Yuji O.Norio N.Ritsuo S.Takeo S. J. Org. Chem. 1988, 53: 2650 - 4c
Iritani K.Yanagihara N.Utimoto K. J. Org. Chem. 1986, 51: 5499 - 4d
Cavicchioli M.Bouyssi D.Gore J.Balme G. Tetrahedron Lett. 1996, 37: 1429 - 4e
Nagarajan A.Balasubramanian TR. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1987, 26: 917 - 4f
Rossi R.Bellina F.Biagetti M.Catanese A.Mannina L. Tetrahedron Lett. 2000, 41: 5281 - 4g
Bouyssi D.Balme G. Synlett 2001, 1191 - 4h
Cacchi S.Delmastro M.Ianelli S.Nardelli M. Gazz. Chim. Ital. 1992, 122: 11 - 4i
Arcadi A.Burini A.Cacchi S.Delmastro M.Marinell F.Pietroni BR. J. Org. Chem. 1992, 57: 976 - 5
Lenders B.Kläui W. Chem. Ber. 1990, 123: 2233 ; and references therein