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Volumn 70, Issue 5, 2005, Pages 1828-1834

Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: Expanding the scope of the Vilsmeier formylation

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMMONIA; FUNGUS RESISTANCE; SYNTHESIS (CHEMICAL);

EID: 14544308311     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0479866     Document Type: Article
Times cited : (80)

References (38)
  • 1
    • 0002556521 scopus 로고    scopus 로고
    • Paquette L. A., Ed.; Wiley: New York
    • (a) Jones, G.; Stanforth, S. P. In Organic Reactions; Paquette L. A., Ed.; Wiley: New York, 1997; Vol. 49, pp 1-330.
    • (1997) Organic Reactions , vol.49 , pp. 1-330
    • Jones, G.1    Stanforth, S.P.2
  • 3
    • 0003412412 scopus 로고    scopus 로고
    • J. Wiley & Sons: New York, and references therein
    • The Vilsmeier formylation has also been applied to alkenes, acetals, and ketals, see: Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 785 and references therein.
    • (2001) Advanced Organic Chemistry, 5th Ed. , pp. 785
    • Smith, M.B.1    March, J.2
  • 6
    • 0033979455 scopus 로고    scopus 로고
    • For recent reviews on cruciferous phytoalexins see: (a) Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q. Phytochemistry 2000, 53, 161. (b) Pedras, M. S. C.; Jha, M.; Ahiahonu, P. W. K. Curr. Org. Chem. 2003, 7, 1635.
    • (2000) Phytochemistry , vol.53 , pp. 161
    • Pedras, M.S.C.1    Okanga, F.I.2    Zaharia, I.L.3    Khan, A.Q.4
  • 7
    • 0141920764 scopus 로고    scopus 로고
    • For recent reviews on cruciferous phytoalexins see: (a) Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q. Phytochemistry 2000, 53, 161. (b) Pedras, M. S. C.; Jha, M.; Ahiahonu, P. W. K. Curr. Org. Chem. 2003, 7, 1635.
    • (2003) Curr. Org. Chem. , vol.7 , pp. 1635
    • Pedras, M.S.C.1    Jha, M.2    Ahiahonu, P.W.K.3
  • 18
    • 84989444646 scopus 로고
    • Indoline-2-thione was prepared following a general procedure for conversion of the carbonyl group to the thione group: Scheeren, J. W.; Ooms, P. H. J.; Nivard, R. J. F. Synthesis 1973, 149.
    • (1973) Synthesis , pp. 149
    • Scheeren, J.W.1    Ooms, P.H.J.2    Nivard, R.J.F.3
  • 19
    • 14544268656 scopus 로고    scopus 로고
    • note
    • 2.
  • 20
    • 14544306148 scopus 로고    scopus 로고
    • note
    • Although the results shown in Table 1 entry 6 represented an improvement in the yield of 12, due to the amount of starting material remaining in the reaction mixture, the additional chromatographic separation required rendered this preparation less efficient.
  • 21
    • 14544271985 scopus 로고    scopus 로고
    • note
    • A number of undetermined products were formed including 2-chloroindole-3-carbaldeheyde (11) in ca. 10%.
  • 22
    • 14544286488 scopus 로고    scopus 로고
    • note
    • Compound 21 was synthesized using the conditions of entry 8, Table 1 followed by water workup instead of ammonia.
  • 23
    • 14544278474 scopus 로고    scopus 로고
    • note
    • For complete spectroscopic data of 19, see ref 8.
  • 27
    • 14544292551 scopus 로고    scopus 로고
    • note
    • Described in the Supporting Information.
  • 33
    • 14544301523 scopus 로고    scopus 로고
    • note
    • 3CN solution as a mixture of E/Z isomers (spectroscopic data in the Supporting Information).
  • 35
    • 0003412412 scopus 로고    scopus 로고
    • J. Wiley & Sons: New York
    • The reaction of ammonia with aldehydes leads to spontaneous polymerization of the resulting imines. (a) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 1186. (b) Hull, W. E.; Sykes, B. D.; Babior, B. M. J. Org. Chem. 1973, 38, 2931.
    • (2001) Advanced Organic Chemistry, 5th Ed. , pp. 1186
    • Smith, M.B.1    March, J.2
  • 36
    • 0041863430 scopus 로고
    • The reaction of ammonia with aldehydes leads to spontaneous polymerization of the resulting imines. (a) Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 1186. (b) Hull, W. E.; Sykes, B. D.; Babior, B. M. J. Org. Chem. 1973, 38, 2931.
    • (1973) J. Org. Chem. , vol.38 , pp. 2931
    • Hull, W.E.1    Sykes, B.D.2    Babior, B.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.