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Volumn 48, Issue 6, 2007, Pages 941-944

Reaction of functionalized azomethine ylides with acetylenic dipolarophiles: the facile synthesis of functionalized 2H- and 1H-pyrroles

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIHYDROPYRROLE; ACETYLENE; ACETYLENE DERIVATIVE; ACETYLENIC DIPOLAROPHILE; AZOMETHINE YLIDE; NITRILE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33846111004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.018     Document Type: Article
Times cited : (16)

References (34)
  • 3
    • 0003607021 scopus 로고    scopus 로고
    • Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds), Pergamon, Oxford, UK 207-257
    • Gribble G.W. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 2 (1996), Pergamon, Oxford, UK 207-257
    • (1996) Comprehensive Heterocyclic Chemistry , vol.2
    • Gribble, G.W.1
  • 9
    • 37049070668 scopus 로고
    • For reviews:
    • For reviews:. Grigg R. Chem. Soc. Rev. 16 (1987) 89-121
    • (1987) Chem. Soc. Rev. , vol.16 , pp. 89-121
    • Grigg, R.1
  • 10
    • 84918190027 scopus 로고
    • Yoshida Z., Shiba T., and Oshiro Y. (Eds), VCH
    • Grigg R. In: Yoshida Z., Shiba T., and Oshiro Y. (Eds). New Aspects of Organic Chemistry I (1989), VCH 113-134
    • (1989) New Aspects of Organic Chemistry I , pp. 113-134
    • Grigg, R.1
  • 19
    • 33846045961 scopus 로고    scopus 로고
    • Kawashima, K.; Kakehi, A.; Noguchi, M. Tetrahedron, in press.
  • 23
    • 33846049949 scopus 로고    scopus 로고
    • note
    • Structures of 2,5-dihydropyrroles 4a, 8a, and 12a and 1H-pyrrole 15a were confirmed by single crystal X-ray structure analysis and their crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 621689 for 4a, CCDC 621692 for 8a, CCDC 621691 for 12a, and CDDC 621693 for 15a copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 24
    • 33846112031 scopus 로고    scopus 로고
    • note
    • 3), 166.81 (5-C).
  • 26
    • 33846077940 scopus 로고    scopus 로고
    • note
    • 3), 168.01 (5-C). Chromatographic separation on silica-gel of 14a from the mixture gave an inseparable mixture of 14a, 13a, and other many products due to the decomposition.
  • 27
    • 33846069622 scopus 로고    scopus 로고
    • note
    • 3): 32.99, 51.52, 51.55, 112.31, 116.40, 123.02, 127.06, 128.96, 129.00, 137.32, 137.48, 164.49, 165.33.
  • 33
    • 0000432199 scopus 로고
    • 3c Therein, the 2H-pyrroles were formed in situ by the DDQ-oxidation of 2,5-dihydropyrroles, which were obtained by the reaction of NH-azomethine ylides with MP. Also, an isomerization process, a sigmatropic rearrangement, of 3H-pyrrole to 2H- and 1H-pyrrole finally through the ester group imigration was discussed:
    • 3c Therein, the 2H-pyrroles were formed in situ by the DDQ-oxidation of 2,5-dihydropyrroles, which were obtained by the reaction of NH-azomethine ylides with MP. Also, an isomerization process, a sigmatropic rearrangement, of 3H-pyrrole to 2H- and 1H-pyrrole finally through the ester group imigration was discussed:. Chiu P.-K., and Sammes M.P. Tetrahedron 46 (1990) 3439-3456
    • (1990) Tetrahedron , vol.46 , pp. 3439-3456
    • Chiu, P.-K.1    Sammes, M.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.