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Volumn 64, Issue 17, 2008, Pages 3674-3686

Synthesis of carbazoles by dehydro Diels-Alder reactions of ynamides

Author keywords

[No Author keywords available]

Indexed keywords

10 TOSYL 10H PHENANTHRO[9,10 B]CARBAZOLE; 10 [(4 METHYLPHENYL}SULFONYL] 10H PYRIDO[3,4 B]CARBAZOLE; 11 CYCLOHEXENYL 5 TOSYL 5H BENZO[B]CARBAZOLE; 12 TOSYL 12H NAPHTHO[1,2 B]CARBAZOLE; 2 METHYL 9 TOSYL 9H CARBAZOLE; 3 CHLORO 9 METHYL 5 [(4 METHYLPHENYL}SULFONYL] 5H BENZO[B]CARBAZOLE; 5 TOSYL 5H BENZO[B]CARBAZOLE; 5 [(4 METHYLPHENYL)SULFONYL] 9 METHOXY 5H BENZO[B]CARBAZOLE; 5 [(4 METHYLPHENYL)SULFONYL] 9 NITRO 5H BENZO[B]CARBAZOLE; 5 [(4 METHYLPHENYL}SULFONYL] 11 TRIMETHYLSILYL 5H BENZO[B]CARBAZOLE; 6 (PYRIMIDIN 2 YL) 5 TOSYL 5H BENZO[B]CARBAZOLE; 6 TOSYL 6H PYRIDO[4,3 B]CARBAZOLE; 7,8,9,10 TETRAHYDRO 5 TOSYL 5H BENZO[B]CARBAZOLE; 7,8,9,10 TETRAHYDRO 6 (TRIMETHYLSILYL) 5 TOSYL 5H BENZO[B]CARBAZOLE; 7,8,9,10 TETRAHYDRO 6 PHENYL 5 TOSYL 5H BENZO[B]CARBAZOLE; 8 TOSYL 8H NAPHTHO[2,1 B]CARBAZOLE; 9 CHLORO 5 [(4 METHYLPHENYL)SULFONYL] 5H BENZO[B]CARBAZOLE; 9 FLUORO 5 [(4 METHYLPHENYL)SULFONYL] 5H BENZO[B]CARBAZOLE; 9 METHOXY 5 METHYLSULFONYL 5H BENZO[B]CARBAZOLE; 9 METHYL 5 METHYLSULFONYL 5H BENZO[B]CARBAZOLE; 9 NITRO 11 PHENYL 5 TOSYL 5H BENZO[B]CARBAZOLE; 9 [(4 METHYLPHENYL}SULFONYL] 9H THIENO[2,3 B]CARBAZOLE; CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 40649124041     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.029     Document Type: Article
Times cited : (55)

References (86)
  • 1
    • 85120282343 scopus 로고
    • (a) D.P. Chakraborty G.A. Cordell The Alkaloids Vol. 44 1993 Academic New York, NY 257
    • (1993) , pp. 257
    • Chakraborty, D.P.1
  • 2
    • 85120285533 scopus 로고
    • (b) H.J. Knölker C.J. Moody Advances in Nitrogen Heterocycles Vol. 1 1995 JAI Greenwich 173
    • (1995) , pp. 173
    • Knölker, H.J.1
  • 4
    • 85120242824 scopus 로고    scopus 로고
    • (d) P.T. Gallagher Science of Synthesis Vol. 10 2000 Thieme Stuttgart p 693
    • (2000)
    • Gallagher, P.T.1
  • 18
    • 85120265351 scopus 로고
    • (d) G.W. Gribble A. Brossi The Alkaloids Vol. 39 1990 Academic New York, NY 239
    • (1990) , pp. 239
    • Gribble, G.W.1
  • 19
    • 85120262124 scopus 로고
    • (e) J. Bergman Atta-ur-Rahman Stereoselective Synthesis (Part A), Studies in Natural Product Chemistry Vol. 1 1988 Elsevier Amsterdam 3
    • (1988) , pp. 3
    • Bergman, J.1
  • 20
    • 85120259382 scopus 로고    scopus 로고
    • For more recent approaches, see:
  • 48
    • 85120276380 scopus 로고    scopus 로고
    • For syntheses of benzo[ b ]carbazoles by related cycloaromatizations of arenyne ketenimines, see:
  • 51
    • 85120256433 scopus 로고    scopus 로고
    • For a pioneer work, see:
  • 53
    • 85120244016 scopus 로고    scopus 로고
    • For recent contributions, see:
  • 57
    • 85120273524 scopus 로고    scopus 로고
    • For our own contributions to dehydro Diels–Alder reactions, see:
  • 66
    • 85120252229 scopus 로고    scopus 로고
    • For the first use of ynamides in intramolecular Diels–Alder reactions, see:
  • 68
    • 85120242692 scopus 로고    scopus 로고
    • For recent applications of ynamides in cycloadditions, see:
  • 72
    • 85120253399 scopus 로고    scopus 로고
    • (e) For a special issue devoted to the chemistry of ynamides, see: Tetrahedron 62 2006
    • (2006) Tetrahedron , vol.62
  • 74
    • 17744371152 scopus 로고    scopus 로고
    • For a related synthesis of indoles and indolines by [4+2] cycloaddition of ynamides to conjugated enynes, see: J.R. Dunetz R.L. Danheiser J. Am. Chem. Soc. 127 2005 5776 5777
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5776-5777
    • Dunetz, J.R.1    Danheiser, R.L.2
  • 75
    • 85120263883 scopus 로고    scopus 로고
    • For a preliminary communications, see:
  • 79
    • 85120263087 scopus 로고    scopus 로고
    • 13b,c
  • 82
    • 85120260234 scopus 로고    scopus 로고
    • 3) of ynamide 1c with p -nitroiodobenzene (1 g, 46%) or 2-iodopyrimidine (1 h, 57%).
  • 84
    • 85120253309 scopus 로고    scopus 로고
    • Electron-poor and electron-rich heteroaroaromatic substrates (e.g., 2h , 2j ) gave low yields in IDDA reactions due to partial decomposition of the reacting intermediates. See Ref.  14 for more details.
  • 85
    • 85120245191 scopus 로고    scopus 로고
    • The starting arylynamides 2k , 2l and 2m were obtained following the same procedure as for 2 ( Scheme 9 ) but starting with 2-iodo-5-chloroaniline and the mesyl-protected analogue of 1i either with TIPS (for 2l ) or TES (for 2m ).
  • 86
    • 85120282038 scopus 로고    scopus 로고
    • Electron-rich and electron-poor para substituents on the reacting aryl ring are very well tolerated in IDDA reactions. Herein, halogenated substrates on the reacting and non-reacting aryl ring (e.g., 2e , 2f and 2k ) underwent IDDA reactions in rather good yields. Mesyl groups in nitrogen (e.g., 2l and 2m ) are also very well tolerated in IDDA reactions. See Refs. 14d,h for more details of the IDDA mechanism.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.