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Volumn 38, Issue 26, 1997, Pages 4535-4538

Mild nitrosation and hydrolysis of polyfunctional amides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BRYOSTATIN; FUNCTIONAL GROUP; VANCOMYCIN;

EID: 0030912448     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00972-6     Document Type: Article
Times cited : (66)

References (37)
  • 2
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    • (c) Singh, L.; Ram, R. N. J. Org. Chem. 1994, 59, 710-711, and references cited therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 710-711
    • Singh, L.1    Ram, R.N.2
  • 6
    • 0028063642 scopus 로고
    • and references cited therein
    • (b) For the cleavage of N-nitrosamides to produce diazoalkanes under physiological conditions, cf. White, E. H.; Paik, S. Tetrahedron Lett. 1994, 35, 7731-7734, and references cited therein.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7731-7734
    • White, E.H.1    Paik, S.2
  • 7
    • 85082675546 scopus 로고
    • and references cited therein
    • For the use of N-nitrosation to activate amides towards nucleophilic attack by thiols and amines, cf. Berenguer, R.; Garcia, J.; Vilarrasa, J. Synthesis 1989, 305-306, and references cited therein.
    • (1989) Synthesis , pp. 305-306
    • Berenguer, R.1    Garcia, J.2    Vilarrasa, J.3
  • 14
    • 0342830645 scopus 로고    scopus 로고
    • note
    • (c) We also examined the use of a tert-butyl amide in this context, and found it to be unsuitable.
  • 16
    • 0342395833 scopus 로고    scopus 로고
    • note
    • 1H NMR, IR, and mass spectral data.
  • 21
    • 0343701090 scopus 로고    scopus 로고
    • note
    • For a discussion of the mechanism of the lithium hydroperoxide cleavage of active esters, cf. ref. 13a.
  • 26
    • 0029964304 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254, and references cited therein.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3251-3254
    • Evans, D.A.1    Watson, P.S.2
  • 30
    • 0342395830 scopus 로고    scopus 로고
    • note
    • 2) conditions. (b) Vilarassa and co-workers have postulated that nitrosation favors the carbamate at short reaction times with nitrogen dioxide, and that these N-nitroso carbamates may be degraded with acid. Thus, nitrosation with nitrogen dioxide in acetic acid for prolonged time favors nitrosation of the amide residue. cf. Ref. 18 for a complete discussion of these results.
  • 34
    • 0342830632 scopus 로고    scopus 로고
    • note
    • 2O and DMAP afforded the opposite selectivity, giving N-Boc N-methylbenzamide and N-Boc benzamide in a 1:9 ratio. To the best of our knowledge, this sense of selectivity has not been documented previously.
  • 35
    • 0027417977 scopus 로고
    • (b) It has been shown that primary amides are nitrosated more readily than hindered (isopropyl) secondary amides: Okuyama, S.; Kamachi, H.; Oki, T. Chem. Pharm. Bull. 1993, 41, 223-225; and Webster, F. X.; Millar, J. G.; Silverstein, R. M. Tetrahedron Lett. 1986, 27, 4941-4944.
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 223-225
    • Okuyama, S.1    Kamachi, H.2    Oki, T.3
  • 36
    • 0000204620 scopus 로고
    • (b) It has been shown that primary amides are nitrosated more readily than hindered (isopropyl) secondary amides: Okuyama, S.; Kamachi, H.; Oki, T. Chem. Pharm. Bull. 1993, 41, 223-225; and Webster, F. X.; Millar, J. G.; Silverstein, R. M. Tetrahedron Lett. 1986, 27, 4941-4944.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4941-4944
    • Webster, F.X.1    Millar, J.G.2    Silverstein, R.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.