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Volumn 2, Issue 15, 2000, Pages 2327-2329

Synthesis of cyclic sulfonamides via intramolecular copper-catalyzed reaction of unsaturated iminoiodinanes

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOAZOBENZENE; AZIRIDINE DERIVATIVE; COPPER; DRUG DERIVATIVE; ENZYME INHIBITOR; FUSED HETEROCYCLIC RINGS; SULFAMIDOCHRYSOIDINE; SULFONAMIDE;

EID: 0034720908     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000130c     Document Type: Article
Times cited : (159)

References (39)
  • 5
    • 0026750833 scopus 로고
    • Drugs Future 1992, 17, 451.
    • (1992) Drugs Future , vol.17 , pp. 451
  • 6
    • 0030814402 scopus 로고    scopus 로고
    • (a) Drugs Future 1997, 22, 341.
    • (1997) Drugs Future , vol.22 , pp. 341
  • 7
    • 0022530944 scopus 로고
    • (b) Drugs Future 1986, 11, 565.
    • (1986) Drugs Future , vol.11 , pp. 565
  • 11
    • 0031838597 scopus 로고    scopus 로고
    • (a) Drugs Future 1998, 23, 365.
    • (1998) Drugs Future , vol.23 , pp. 365
  • 16
    • 84865797090 scopus 로고
    • (d) Chem. Abstr. 1985, 102, 78901p.
    • (1985) Chem. Abstr. , vol.102 , pp. 78901
  • 17
    • 4243417170 scopus 로고
    • U.S. Patent 4,842,639, 1989
    • (e) Pasteris, R. J. U.S. Patent 4,842,639, 1989; Chem. Abstr. 1990, 112, 179032t.
    • (1990) Chem. Abstr. , vol.112
    • Pasteris, R.J.1
  • 35
    • 85037506746 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra in which aromatic protons of the iodobenzene moiety were observed together with the disappearance of those of the sulfonamide function and the upfield shift of the alkane protons. For example, for the iminoiodinane derived from sulfonamide 9c: δ 1.26 (m, 2H), 1.76 (m, 2H), 2.00 (m, 2H), 4.95 (m, 2H), 5.64 (m, 1H), 7.39 (m, 2H), 7.54 (m, 1H), 7.96 (d, 1H).
  • 36
    • 85037493872 scopus 로고    scopus 로고
    • note
    • The iodinanes were used as soon as they were isolated in order to optimize the yield of the aziridination. However, they could be stored at 4 °C under argon for several days. Their stability is therefore comparable to that of PhINTs or PhINSes.
  • 37
    • 0032577010 scopus 로고    scopus 로고
    • To the best of our knowledge, there is only one example of the preparative use of such a Cu-catalyzed C-H insertion: Overman, L. E.; Tomasi, A. L. J. Am. Chem. Soc. 1998, 120, 4039. In other cases, such compounds were isolated as minor byproducts. For example, see: (a) ref 15. (b) Albone, D. P.; Aujla, P. S.; Taylor, P. C.; Challenger, S., Derrick, A. M. J. Org. Chem. 1998, 63, 9569.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4039
    • Overman, L.E.1    Tomasi, A.L.2
  • 38
    • 0032509247 scopus 로고    scopus 로고
    • (a) ref 15
    • To the best of our knowledge, there is only one example of the preparative use of such a Cu-catalyzed C-H insertion: Overman, L. E.; Tomasi, A. L. J. Am. Chem. Soc. 1998, 120, 4039. In other cases, such compounds were isolated as minor byproducts. For example, see: (a) ref 15. (b) Albone, D. P.; Aujla, P. S.; Taylor, P. C.; Challenger, S., Derrick, A. M. J. Org. Chem. 1998, 63, 9569.
    • (1998) J. Org. Chem. , vol.63 , pp. 9569
    • Albone, D.P.1    Aujla, P.S.2    Taylor, P.C.3    Challenger, S.4    Derrick, A.M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.