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Synthesis 2001(9): 1363-1367
DOI: 10.1055/s-2001-15223
DOI: 10.1055/s-2001-15223
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Polyhydroxylated Derivatives of Phenyl Vinyl Sulfone as Structural Analogs of Chalcones
Further Information
Received
20 November 2000
Publication Date:
24 September 2004 (online)
Publication History
Publication Date:
24 September 2004 (online)
Abstract
A series of polyhydroxylated phenyl vinyl sulfones was prepared by phase transfer condensation of suitable phenyl methyl sulfones with substituted benzaldehydes. The compounds were prepared as structural analogs of biologically active chalcones. One of the compounds was cyclized to a derivative of 2,3-dihydro-2-phenyl-1,4-benzoxathiin-4,4-dioxide, a heterocyclic system closely resembling flavanones.
Key words
phenyl vinyl sulfones - 1,4-benzoxathiin-4,4-dioxide - chalcones - flavanones
- 1
Dhar DN. The Chemistry of Chalcones and Related Compounds Wiley; New York: 1981. - 2
Hsieh HK.Lee TH.Wang JP.Wang JJ.Lin CN. Pharm. Res. 1998, 15: 39 - 3
Lin CN.Lee TH.Hsu MF.Wang JP.Ko FN.Teng CM. J. Pharm. Pharmacol. 1997, 49: 530 - 4
Powers DG.Casebier DS.Fokas D.Ryan WR.Troth JR.Coffen DL. Tetrahedron 1998, 54: 4085 - 5
Simpkins NS. Sulphones in Organic Synthesis Pergamon Press; Oxford: 1993. - 6
The Chemistry of Sulphones and Sulphoxides
Patai S.Rappoport Z.Stirling C. Wiley; Chichester: 1988. - 7
Simpkins NS. Tetrahedron 1990, 46: 6951 - 8
Magnus PD. Tetrahedron 1977, 33: 2019 -
9a
Reddy PE, andReddy RMV. inventors; PCT Int. Appl. WO9918068. -
-
10a
Konopa JK,Konieczny MT,Horowska BJ,Kunikowski AJ,Asao T,Nishino H, andYamada Y. inventors; Jpn. Patent JP 9003037. -
- 11
Pathak D.Pathak K.Singla AK. Fitoterapia 1991, 62: 371 - 12
Das A.Wang JH.Lien EJ. Prog. Drug Res. 1994, 42: 134 - 13
Sogawa S.Nihro Y.Ueda H.Izumi A.Miki T.Matsumoto H.Satoh TJ. Med. Chem. 1993, 36: 3904 - 14
Miyahara M.Ohtaka H.Katayama H.Tatsumi Y.Miyaichi Y.Tomimori T. Yakugaku Zasshi 1993, 113: 133 - 15
Konieczny MT.Horowska B.Kunikowski A.Konopa J.Wierzba K.Yamada Y.Asao T. J. Org. Chem. 1999, 64: 359 -
16a
Konopa JK,Konieczny MT,Horowska BJ,Kunikowski AJ,Asao T,Nishino H, andYamada Y. inventors; Jpn. Patent JP 9025278. -
- 17
Cardillo G.Savoia D.Umano-Ronchi A. Synthesis 1975, 453 - 18
Baliah V.Ganapathy K.Ananthapadmanabhan S. Indian J. Chem., Sect. B 1982, 21: 208 - 19
Julia M.Righini A.Uguen D. J. Chem. Soc., Perkin Trans. 1 1978, 1646 - 20
Reddy MVR.Reddy S. Sulfur Lett. 1987, 7: 43 - 21
Reddy DB.Murthy KR.Seshamna T. Sulfur Lett. 1990, 12: 73 - 22
Villemin D.Ben Alloum A. Synth. Commun. 1991, 21: 63 - 23
Walker J. J. Chem. Soc. 1945, 630 - 24
Scribner RM. J. Org. Chem. 1966, 31: 3671 - 25
Pagani G.Maiorana S. Chim. Ind. (Milan) 1971, 53: 468 - 26
Parham WE.Willette GL. J. Org. Chem. 1960, 25: 53 - 27
Parham WE.Jones JD. J. Am. Chem. Soc. 1954, 76: 1068 - 28
Cao S.Fan A.Huang Z.Zhang Z. Synth. Commun. 1996, 26: 3979 -
29a
Cao S.Zhang Z. Huaxue Shiji 1999, 21: 176