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Volumn 10, Issue 6, 2008, Pages 1071-1074

Preparation of the isomeric azaindoline family by intramolecular carbolithiation

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; INDOLINE; LITHIUM;

EID: 45549105078     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702862d     Document Type: Article
Times cited : (24)

References (38)
  • 1
    • 58149169590 scopus 로고    scopus 로고
    • For reviews, see: (a) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; 3, Mechanisms of Importance in Synthesis; JAI Press: Greenwich, CT, 1994; pp 251-273.
    • For reviews, see: (a) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; Vol. 3, Mechanisms of Importance in Synthesis; JAI Press: Greenwich, CT, 1994; pp 251-273.
  • 6
    • 58149169597 scopus 로고    scopus 로고
    • Azaindoline is used here to describe the pyrrolopyridine system; thus, 4-azaindoline is 2, 3-dihydro-1H-pyrrolo[3, 2-b]pyridine, 5-azaindoline is 2, 3-dihydro-1H-pyrrolo[3, 2-c]pyridine, 6-azaindoline is 2, 3-dihydro-1H-pyrrolo- [2, 3-c]pyridine, and 7-azaindoline is 2, 3-dihydro-1H-pyrrolo[2, 3-b]pyridine.
    • Azaindoline is used here to describe the pyrrolopyridine system; thus, 4-azaindoline is 2, 3-dihydro-1H-pyrrolo[3, 2-b]pyridine, 5-azaindoline is 2, 3-dihydro-1H-pyrrolo[3, 2-c]pyridine, 6-azaindoline is 2, 3-dihydro-1H-pyrrolo- [2, 3-c]pyridine, and 7-azaindoline is 2, 3-dihydro-1H-pyrrolo[2, 3-b]pyridine.
  • 8
    • 58149151950 scopus 로고    scopus 로고
    • Kruber, O. Chem. Ber. 1943, 76, 128.
    • (a) Kruber, O. Chem. Ber. 1943, 76, 128.
  • 11
    • 0014244981 scopus 로고
    • The Pyrrolopyridines
    • Katritzky, A. R, Boulton, A. J, Eds, Academic Press: New York
    • (d) Willette, R. E. Monoazaindolines: The Pyrrolopyridines. In Adv. In Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York 1968; Vol. 9, pp 27-105.
    • (1968) Adv. In Heterocyclic Chemistry , vol.9 , pp. 27-105
    • Willette, R.E.M.1
  • 35
    • 0000401303 scopus 로고    scopus 로고
    • 2-Amino-3-bromopyridine, 3-amino-4-bromopyridine and 4-amino-3- bromopyridine, see: Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1999, 1, 1505.
    • 2-Amino-3-bromopyridine, 3-amino-4-bromopyridine and 4-amino-3- bromopyridine, see: Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1999, 1, 1505.
  • 36
    • 0034752296 scopus 로고    scopus 로고
    • 3-Amino-2-bromopyridine, see: Cañibano, V.; Rodríguez, J. F.; Santos, M.; Sanz-Tejedor, M. A.; Carreño, M. C.; González, G.; García-Ruano, J. L. Synthesis 2001, 14, 2175.
    • 3-Amino-2-bromopyridine, see: Cañibano, V.; Rodríguez, J. F.; Santos, M.; Sanz-Tejedor, M. A.; Carreño, M. C.; González, G.; García-Ruano, J. L. Synthesis 2001, 14, 2175.
  • 38
    • 58149146311 scopus 로고    scopus 로고
    • It is likely that the proton transfer is an intermolecular process catalyzed by a small quanity of 1-allyl-3-methyl-7-azaindoline peresent in the reaction mixture as a consequence of inadvertent quench of 9, by solvent or adventitious acid. Thus: 9, 1-allyl-3-methyl-7-azaindoline → 1-allyl-3-methyl-7-azaindoline, 10
    • It is likely that the proton transfer is an intermolecular process catalyzed by a small quanity of 1-allyl-3-methyl-7-azaindoline peresent in the reaction mixture as a consequence of inadvertent quench of 9, by solvent or adventitious acid. Thus: 9, + 1-allyl-3-methyl-7-azaindoline → 1-allyl-3-methyl-7-azaindoline + 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.