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Volumn 17, Issue 8-9 I, 2003, Pages 1482-1486

Environmentally benign synthesis of isoflavone derivatives using polymer-supported hypervalent iodine(III) reagent

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID DERIVATIVE; CHALCONE DERIVATIVE; IODINE; IODOBENZENE; ISOFLAVONE DERIVATIVE; METHANOL; MONOMER; POLYMER; POLY[4 (DIACETOXY)IODO]STYRENE; REAGENT; SULFONIC ACID DERIVATIVE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG; [HYDROXY(TOSYLOXY)IODO]BENZENE;

EID: 0038440566     PISSN: 02179792     EISSN: None     Source Type: Journal    
DOI: 10.1142/s0217979203019198     Document Type: Conference Paper
Times cited : (6)

References (19)
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    • R. M. Moriarty, J. S. Khosrowshahi and O. Prakash, Tetrahedron Lett. 26, 2961 (1985); G. F. Koser and R. H. Wettach, J. Org. Chem. 41, 3609 (1976).
    • (1976) J. Org. Chem. , vol.41 , pp. 3609
    • Koser, G.F.1    Wettach, R.H.2
  • 10
    • 85064718268 scopus 로고
    • Y. Miki, S. Kobayashi and H. Hachiken, Synlett. 1001 (1994); Y. Miki, R. Fujita, K. Matsushita, J. Chem Soc., Perkin Trans 1, 2533 (1998).
    • (1994) Synlett. , pp. 1001
    • Miki, Y.1    Kobayashi, S.2    Hachiken, H.3
  • 13
    • 0003115609 scopus 로고    scopus 로고
    • H. Togo, G. Nogami and M. Yokoyama, Synlett. 534 (1998); H. Togo, S. Abe, G. Nogami and M. Yokoyama, Bull. Chem. Soc. Jpn. 72, 2351 (1999).
    • (1998) Synlett. , pp. 534
    • Togo, H.1    Nogami, G.2    Yokoyama, M.3
  • 15
  • 17
    • 0035819291 scopus 로고    scopus 로고
    • H. Tohma, H. Morioka, S. Takizawa, M. Arisawa and Y. Kita, Tetrahedron 57, 345 (2001); Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakuraiand S. Oka, J. Am. Chem. Soc. 116, 3684 (1994).
    • (2001) Tetrahedron , vol.57 , pp. 345
    • Tohma, H.1    Morioka, H.2    Takizawa, S.3    Arisawa, M.4    Kita, Y.5
  • 19
    • 0038557485 scopus 로고    scopus 로고
    • note
    • Although we have not yet elaborated on the rearrangement mechanism to afford acetals 2, the argument mentioned by Moriarty and his coworkers is suggestive and it seems to be persuasive. Both the hypervalent iodine(III) and the thallium reagents are so-called soft reagents. The C=C double bond of the chalcone 1 is, therefore, susceptible to addition of the reagents. After addition of methoxide at the β-position of the bond, the B ring of 1 would migrate to the α-position and the simultaneous addition of another methoxide occurs with concomitant loss of the iodine reagent.


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