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Volumn 9, Issue 19, 2007, Pages 3805-3807

Substitution and cyclization reactions involving the quasi-antiaromatic 2H-indol-2-one ring system

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; MACROCYCLIC COMPOUND;

EID: 34848889987     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7016438     Document Type: Article
Times cited : (71)

References (45)
  • 11
    • 34848884475 scopus 로고    scopus 로고
    • Academic Press: London, UK
    • Sundberg, R. J. Indoles; Academic Press: London, UK, 1996; Vol. 17, pp 152-154.
    • (1996) Indoles , vol.17 , pp. 152-154
    • Sundberg, R.J.1
  • 12
    • 34848863636 scopus 로고    scopus 로고
    • Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; Chapter 8G.
    • (a) Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; Chapter 8G.
  • 38
    • 34848819691 scopus 로고    scopus 로고
    • A reviewer has pointed out that while the mechanism shown in Scheme 2 is not unreasonable, there is no real evidence for the proposed electrophilic addition of 2 to alkenes. An alternative possibility could involve an initial dehydration of 1 with acid to produce a reactive benzylic cation that would then undergo stepwise addition of styrene to eventually give 6. We found, however, that the N-methyl analogue of 1 did not undergo the substitution reaction with styrene and this observation provides good support for the requirement of a 2H-indol-2-one intermediate (i.e. 2).
    • A reviewer has pointed out that while the mechanism shown in Scheme 2 is not unreasonable, there is no real evidence for the proposed electrophilic addition of 2 to alkenes. An alternative possibility could involve an initial dehydration of 1 with acid to produce a reactive benzylic cation that would then undergo stepwise addition of styrene to eventually give 6. We found, however, that the N-methyl analogue of 1 did not undergo the substitution reaction with styrene and this observation provides good support for the requirement of a 2H-indol-2-one intermediate (i.e. 2).
  • 41
    • 0035594725 scopus 로고    scopus 로고
    • Da Silva, J, F. M.; Garden, S. J.; Pinto, A. C. J. Braz Chem. Soc. 2001, 273.
    • (b) Da Silva, J, F. M.; Garden, S. J.; Pinto, A. C. J. Braz Chem. Soc. 2001, 273.
  • 45
    • 84868263856 scopus 로고    scopus 로고
    • Identical products were obtained in essentially the same yield by carrying out the intramolecular cyclization reaction with catalytic ptoluenesulfonic acid in toluene at 100 °C
    • Identical products were obtained in essentially the same yield by carrying out the intramolecular cyclization reaction with catalytic ptoluenesulfonic acid in toluene at 100 °C


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.