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Synthesis 2002(18): 2701-2706
DOI: 10.1055/s-2002-35984
DOI: 10.1055/s-2002-35984
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2H-1-benzopyran-2-ones
Further Information
Received
9 September 2002
Publication Date:
06 December 2002 (online)
Publication History
Publication Date:
06 December 2002 (online)
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Abstract
Halogen acid-catalysed deprotection and cyclisation of Baylis-Hillman products obtained using O-benzylated salicylaldehyde precursors has been shown to afford 3-(halomethyl)coumarins (3-halomethyl-2H-1-benzopyran-2-ones) chemoselectively and in good yield.
Key words
heterocycles - synthesis - coumarins - 2H-1-benzopyran-2-ones - Baylis-Hillman reaction
- 1
Murray RDH. In Progress in the Chemistry of Natural ProductsHerz W.Grisebach H.Kirby GW. Springer; New York: 1978. p.199-429 -
2a
Periers A.-M.Laurin P.Benedetti Y.Lachaud S.Ferroud D.Iltis A.Haesslein J.-L.Klich M.L’Hermite G.Musicki B. Tetrahedron Lett. 2000, 41: 867 -
2b
Peixoto C.Laurin P.Klich M.Dupuis-Hamelin C.Mauvais P.Lassaigne P.Bonnefoy A.Musicki B. Tetrahedron Lett. 2000, 41: 1741 -
3a
Hermodson MA.Barker WM.Link KP. J. Med. Chem. 1971, 14: 167 -
3b
Conlin GM.Gear JR. J. Nat. Prod. 1993, 56: 1402 - 4
Fuller RW.Bokesch HR.Gustafson KR.McKee TC.Cardellina JH.McMahon JB.Cragg GM.Soejarto DD.Boyd MR. Bioinorg. Med. Chem. Lett. 1994, 4: 1961 - 5
Zhao H.Neamati N.Hong H.Mazumder A.Wang S.Sunder S.Milne GWA.Pommier Y.Burke TR. J. Med. Chem. 1997, 40: 242 - 6
Hariprasad V.Talele TT.Kulkarni VM. Pharm. Pharmacol. Commun. 1998, 4: 365 - 7
John EVO.Israelstam SS. J. Org. Chem. 1961, 26: 240 - 8
Panetta JA.Rapoport H. J. Org. Chem. 1982, 47: 946 - 9
Mali RS.Yadav VJ. Synthesis 1977, 464 - 10
Hepworth JD. In Comprehensive Heterocyclic Chemistry Vol. 3:Boulton AJ.McKillop A. Pergamon; Oxford: 1984. p.881 - 11
Bogdal D. J. Chem. Res., Synop 1998, 468 - 12
Fall Y.Teran C.Teijeira M.Santana L.Uriarte E. Synthesis 2000, 643 - 13
Bode ML.Kaye PT. J. Chem Soc., Perkin Trans 1 1990, 2612 - 14
Familoni OB.Kaye PT.Klaas PJ. Chem. Commun. 1998, 2563 - 15
Kaye PT.Nocanda XW. Synthesis 2001, 2389 - 16
Kaye PT.Robinson RS. Synth. Commun. 1996, 26: 2085 -
17a
Bacsa J.Kaye PT.Robinson RS. S. Afr. J. Chem. 1998, 51: 47 -
17b
Bode ML.English RB.Kaye PT. S. Afr. J. Chem. 1992, 45: 25 -
18a
Kaye PT.Nocanda XW. J. Chem. Soc., Perkin.Trans. 1 2000, 1331 -
18b
Kaye PT.Nocanda XW. J. Chem. Soc., Perkin.Trans. 1 2002, 1318 - 20
Drewes SE.Njamela OL.Emslie ND.Ramesar N.Field JS. Synth. Commun. 1993, 23: 2807
References
Kaye, P.T.; Musa, M.A. Synth. Commun., in press (SC-2002-051).
21Athough an allylic displacement (SN′) pathway cannot be excluded, there are some precedents for the addition-elimination sequence outlined in Scheme [2] . See Ref. [15] for further comment.