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Volumn 7, Issue 11, 2005, Pages 2213-2216

Synthesis of carbazoles from ynamides by intramolecular dehydro Diels-Alder reactions

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBAZOLE DERIVATIVE;

EID: 20444488122     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050609a     Document Type: Article
Times cited : (104)

References (70)
  • 1
    • 77957036993 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • (a) Chakraborty, D. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, p 257.
    • (1993) The Alkaloids , vol.44 , pp. 257
    • Chakraborty, D.P.1
  • 42
    • 17744371152 scopus 로고    scopus 로고
    • For a related synthesis of indoles and indolines via [4 + 2] cycloaddition of ynamides and conjugated enynes, see Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5776
    • Dunetz, J.R.1    Danheiser, R.L.2
  • 43
    • 0032524185 scopus 로고    scopus 로고
    • (a) For reviews on carbazoles and benzannulated carbazoles, see ref 6a,e. (b) For syntheses of benzo[b]carbazoles via related cycloaromatizations of arenyne ketenimines, see Shi, C.; Wang, K. K. J. Org. Chem. 1998, 63, 3517
    • (1998) J. Org. Chem. , vol.63 , pp. 3517
    • Shi, C.1    Wang, K.K.2
  • 45
    • 20444464618 scopus 로고    scopus 로고
    • see ref 7e
    • (c) For a recent synthesis of benzo[a]-carbazoles, see ref 7e.
  • 46
    • 20444496254 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 53
    • 77957084049 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Gribble, G. W. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1990; Vol 39, p 239.
    • (1990) The Alkaloids , vol.39 , pp. 239
    • Gribble, G.W.1
  • 64
    • 20444499933 scopus 로고    scopus 로고
    • note
    • Obtained following the same procedure as for 1 (Scheme 2) but starting with 4-amino-3-bromopyridine.
  • 65
    • 20444475521 scopus 로고    scopus 로고
    • note
    • Prepared in 51% yield by treatment of 5c with BrCN in the presence of KH.
  • 68
    • 20444448275 scopus 로고    scopus 로고
    • note
    • In fact, electron-rich substrates, gave complex mixtures showing that, most likely, the cycloaddition is not regioselective.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.