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Volumn 39, Issue 3, 2009, Pages 531-543

Synthesis of 3-indolylpyrroles via base-mediated cycloaddition of TOSMIC with activated indole-2/3-vinylenes

Author keywords

1,3 dipolar cycloaddition; Dictyodendrin; Indole 2 3 vinylenes; Indolyl vinyl ester; Indolylpyrroles

Indexed keywords

3 INDOLYLPYRROLE DERIVATIVE; INDOLE 2 VINYLENE DERIVATIVE; INDOLE 3 VINYLENE DERIVATIVE; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; REAGENT; TOSYLMETHYLISOCYANIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 61649126926     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802406703     Document Type: Article
Times cited : (10)

References (27)
  • 1
    • 0000498308 scopus 로고
    • A new and simple synthesis of the pyrrole ring system from Michael acceptors and tosylmethylisocyanides
    • van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Leusen, D. A new and simple synthesis of the pyrrole ring system from Michael acceptors and tosylmethylisocyanides. Tetrahedron Lett. 1972, 52, 5337-5340.
    • (1972) Tetrahedron Lett , vol.52 , pp. 5337-5340
    • van Leusen, A.M.1    Siderius, H.2    Hoogenboom, B.E.3    van Leusen, D.4
  • 3
    • 0035945771 scopus 로고    scopus 로고
    • Oxazole synthesis with minimal purification: Synthesis and application of a ROMPgel tosmic reagent
    • (b) Barret, A. G. M.; Cramp, S. M.; Hennessy, A. J.; Procopiou, P. A.; Roberts, R. S. Oxazole synthesis with minimal purification: Synthesis and application of a ROMPgel tosmic reagent. Org. Lett. 2001, 3, 271-273;
    • (2001) Org. Lett , vol.3 , pp. 271-273
    • Barret, A.G.M.1    Cramp, S.M.2    Hennessy, A.J.3    Procopiou, P.A.4    Roberts, R.S.5
  • 5
    • 0042280366 scopus 로고    scopus 로고
    • A versatile protocol for the synthesis of oxazole and 3-nitro/3-carbethoxy pyrrole C-nucleosides using TOSMIC
    • (d) Krishna, P. R.; Reddy, V. V. R.; Sharma, G. V. M. A versatile protocol for the synthesis of oxazole and 3-nitro/3-carbethoxy pyrrole C-nucleosides using TOSMIC. Synlett. 2003, 1619-1622;
    • (2003) Synlett , pp. 1619-1622
    • Krishna, P.R.1    Reddy, V.V.R.2    Sharma, G.V.M.3
  • 6
    • 23044435339 scopus 로고    scopus 로고
    • A two-stage iterative process for the synthesis of poly-oxazoles
    • (e) Atkins, J. M.; Vedejs, E. A two-stage iterative process for the synthesis of poly-oxazoles. Org. Lett. 2005, 7, 3351-3354.
    • (2005) Org. Lett , vol.7 , pp. 3351-3354
    • Atkins, J.M.1    Vedejs, E.2
  • 7
    • 0025890323 scopus 로고
    • An efficient synthesis of 3-nitropyrroles
    • (a) van Leusen, D.; Flentge, E.; van Leusen, A. M. An efficient synthesis of 3-nitropyrroles. Tetrahedron 1991, 47, 4639-4644;
    • (1991) Tetrahedron , vol.47 , pp. 4639-4644
    • van Leusen, D.1    Flentge, E.2    van Leusen, A.M.3
  • 8
    • 0030443743 scopus 로고    scopus 로고
    • Alkylation of β-(hydroxymethyl) pyrroles: A new synthesis of porphobilinogen and other trisubstituted pyrroles for photodynamic therapy
    • (b) De Leon, C. Y.; Ganem, B. Alkylation of β-(hydroxymethyl) pyrroles: A new synthesis of porphobilinogen and other trisubstituted pyrroles for photodynamic therapy. J. Org. Chem. 1996, 61, 8730-8731;
    • (1996) J. Org. Chem , vol.61 , pp. 8730-8731
    • De Leon, C.Y.1    Ganem, B.2
  • 9
    • 0000109604 scopus 로고    scopus 로고
    • A Direct synthesis of 2-(trimethylstannyl) pyrroles from Michael acceptors and stannylated tosylmethyl isocyanide
    • (c) Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. A Direct synthesis of 2-(trimethylstannyl) pyrroles from Michael acceptors and stannylated tosylmethyl isocyanide. J. Org. Chem. 1998, 63, 5332-5338;
    • (1998) J. Org. Chem , vol.63 , pp. 5332-5338
    • Dijkstra, H.P.1    ten Have, R.2    van Leusen, A.M.3
  • 10
    • 0037067523 scopus 로고    scopus 로고
    • One-pot synthesis of 3,4-disubstituted 1H-pyrroles from 2-tropanones
    • (d) Airaksinen, A. J.; Ahlgren, M.; Vepsäläinen, J. One-pot synthesis of 3,4-disubstituted 1H-pyrroles from 2-tropanones. J. Org. Chem. 2002, 67, 5019-5021;
    • (2002) J. Org. Chem , vol.67 , pp. 5019-5021
    • Airaksinen, A.J.1    Ahlgren, M.2    Vepsäläinen, J.3
  • 11
    • 33747381269 scopus 로고    scopus 로고
    • Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole weinreb amides
    • (e) Coffin, A. R.; Roussell, M. A.; Tserlin, E.; Pelkey, E. T. Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole weinreb amides. J. Org. Chem. 2006, 71, 6678-6681.
    • (2006) J. Org. Chem , vol.71 , pp. 6678-6681
    • Coffin, A.R.1    Roussell, M.A.2    Tserlin, E.3    Pelkey, E.T.4
  • 12
    • 0000113304 scopus 로고
    • Base-induced cycloaddition of sulfonylmethyl isocyanides to C,N double bonds: Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl chlorides
    • (a) van Leusen, A. M.; Wilderman, J.; Oldenziel, O. H. Base-induced cycloaddition of sulfonylmethyl isocyanides to C,N double bonds: Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl chlorides. J. Org. Chem. 1977, 42, 1153-1159;
    • (1977) J. Org. Chem , vol.42 , pp. 1153-1159
    • van Leusen, A.M.1    Wilderman, J.2    Oldenziel, O.H.3
  • 13
    • 0034629166 scopus 로고    scopus 로고
    • An investigation of imidazole and oxazole syntheses using aryl-substituted TosMIC reagents
    • (b) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. An investigation of imidazole and oxazole syntheses using aryl-substituted TosMIC reagents. J. Org. Chem. 2000, 65, 1516-1524.
    • (2000) J. Org. Chem , vol.65 , pp. 1516-1524
    • Sisko, J.1    Kassick, A.J.2    Mellinger, M.3    Filan, J.J.4    Allen, A.5    Olsen, M.A.6
  • 14
    • 84981662661 scopus 로고
    • Synthesis of 1,3-thiazoles from carbon disulfide and tosylmethyl isocyanide under phase-transfer conditions
    • (a) van Leusen, A. M.; Wildeman, J. Synthesis of 1,3-thiazoles from carbon disulfide and tosylmethyl isocyanide under phase-transfer conditions. Synthesis 1977, 501-502;
    • (1977) Synthesis , pp. 501-502
    • van Leusen, A.M.1    Wildeman, J.2
  • 15
    • 37049080454 scopus 로고
    • Synthesis of 2′-deoxy-β-D-ribofuranosyl imidazole and thiazole C-nucleosides
    • (b) Bergstrom, D. E.; Zhang, P.; Zhou, J. Synthesis of 2′-deoxy-β-D-ribofuranosyl imidazole and thiazole C-nucleosides. J. Chem. Soc., Perkin Trans. 1, 1994, 3029-3034.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 3029-3034
    • Bergstrom, D.E.1    Zhang, P.2    Zhou, J.3
  • 16
    • 0037015447 scopus 로고    scopus 로고
    • Smith, N. D.; Huang, D.; Cosford, N. D. P. One-step synthesis of 3-aryl- and 3,4-diaryl-(1H)-pyrroles using tosylmethyl isocyanide (TOSMIC). Org. Lett. 2002, 4, 3537-3539.
    • Smith, N. D.; Huang, D.; Cosford, N. D. P. One-step synthesis of 3-aryl- and 3,4-diaryl-(1H)-pyrroles using tosylmethyl isocyanide (TOSMIC). Org. Lett. 2002, 4, 3537-3539.
  • 17
    • 33846995686 scopus 로고    scopus 로고
    • An efficient highly regioselective synthesis of 2,3,4-trisubstituted pyrroles by cycloaddition of polarized ketene S,S- and N,S-acetals with activated methylene isocyanides
    • (a) Misra, N. C.; Panda, K.; Ila, H.; Junjappa, H. An efficient highly regioselective synthesis of 2,3,4-trisubstituted pyrroles by cycloaddition of polarized ketene S,S- and N,S-acetals with activated methylene isocyanides. J. Org. Chem. 2007, 72, 1246-1251.
    • (2007) J. Org. Chem , vol.72 , pp. 1246-1251
    • Misra, N.C.1    Panda, K.2    Ila, H.3    Junjappa, H.4
  • 18
    • 0001074332 scopus 로고
    • Synthesis of carbazole alkaloids hyellazole and 6-chlorohyellazole
    • (a) Kano, S.; Sugino, E.; Shibuya, S.; Hibino, S. Synthesis of carbazole alkaloids hyellazole and 6-chlorohyellazole. J. Org. Chem. 1981, 46, 3856-3859;
    • (1981) J. Org. Chem , vol.46 , pp. 3856-3859
    • Kano, S.1    Sugino, E.2    Shibuya, S.3    Hibino, S.4
  • 19
    • 0000573745 scopus 로고
    • Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2
    • (b) Hibino, S.; Sugino, E.; Kuwada, T.; Ogura, N.; Sato, K.; Chosi, T. Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2. J. Org. Chem. 1992, 57, 5917-5921;
    • (1992) J. Org. Chem , vol.57 , pp. 5917-5921
    • Hibino, S.1    Sugino, E.2    Kuwada, T.3    Ogura, N.4    Sato, K.5    Chosi, T.6
  • 20
    • 0028902795 scopus 로고
    • A Versatile construction of the 8H-quinol(4,3-b)carbazole ring system as a potential DNA binder
    • (c) Mohanakrishnan, A. K.; Srinivasan, P. C. A Versatile construction of the 8H-quinol(4,3-b)carbazole ring system as a potential DNA binder. J. Org. Chem. 1995, 60, 1939-1946;
    • (1995) J. Org. Chem , vol.60 , pp. 1939-1946
    • Mohanakrishnan, A.K.1    Srinivasan, P.C.2
  • 21
    • 18844365141 scopus 로고    scopus 로고
    • A novel synthesis of N-protected carbazoles involving electrocyclization of in situ generated enamines
    • (d) Mohanakrishnan, A. K.; Balamurugan, R. A novel synthesis of N-protected carbazoles involving electrocyclization of in situ generated enamines. Tetrahedron Lett. 2005, 46, 4045-4048.
    • (2005) Tetrahedron Lett , vol.46 , pp. 4045-4048
    • Mohanakrishnan, A.K.1    Balamurugan, R.2
  • 23
    • 12944298265 scopus 로고    scopus 로고
    • Reaction of 3/2-formylindoles with TOSMIC: Formation of indolyloxazoles and stable indolyl primary enamines
    • Chakrabarty, M.; Basak, R.; Harigaya, Y.; Takayanagi, H. Reaction of 3/2-formylindoles with TOSMIC: Formation of indolyloxazoles and stable indolyl primary enamines. Tetrahedron 2005, 61, 1793-1801.
    • (2005) Tetrahedron , vol.61 , pp. 1793-1801
    • Chakrabarty, M.1    Basak, R.2    Harigaya, Y.3    Takayanagi, H.4
  • 24
    • 0034687205 scopus 로고    scopus 로고
    • Reaction of 2-Bromomethylazoles and TosMIC: A domino process to azolopyrimidines: Synthesis of core tricycle of the variolins alkaloids
    • (a) Mendiola, J.; Minguez, J. M.; Alvarez-Builla, J.; Vaquero, J. Reaction of 2-Bromomethylazoles and TosMIC: A domino process to azolopyrimidines: Synthesis of core tricycle of the variolins alkaloids. J. Org. Lett. 2000, 2, 3253-3256;
    • (2000) J. Org. Lett , vol.2 , pp. 3253-3256
    • Mendiola, J.1    Minguez, J.M.2    Alvarez-Builla, J.3    Vaquero, J.4
  • 25
    • 3543010787 scopus 로고    scopus 로고
    • Reaction of bromomethylazoles and tosylmethyl isocyanide: A novel heterocyclization method for the syntesis of the core of marine alkaloids variolins and related azolopyrimidines
    • (b) Mendiola, J.; Baeza, A.; Alvarez-Builla, J.; Vaquero, J. J. Reaction of bromomethylazoles and tosylmethyl isocyanide: A novel heterocyclization method for the syntesis of the core of marine alkaloids variolins and related azolopyrimidines. J. Org. Chem. 2004, 69, 4974-4983;
    • (2004) J. Org. Chem , vol.69 , pp. 4974-4983
    • Mendiola, J.1    Baeza, A.2    Alvarez-Builla, J.3    Vaquero, J.J.4
  • 26
    • 20344380447 scopus 로고    scopus 로고
    • Heterocyclizations with tosylmethyl isocyanides derivatives: A new approach to substituted azolopyrimidines
    • (c) Baeza, A.; Mendiola, J.; Burgos, C.; Alvarez-Builla, J.; Vaquero, J. J. Heterocyclizations with tosylmethyl isocyanides derivatives: A new approach to substituted azolopyrimidines. J. Org. Chem. 2005, 70, 4879-4882.
    • (2005) J. Org. Chem , vol.70 , pp. 4879-4882
    • Baeza, A.1    Mendiola, J.2    Burgos, C.3    Alvarez-Builla, J.4    Vaquero, J.J.5
  • 27
    • 0030960259 scopus 로고    scopus 로고
    • An efficient method for the synthesis of 3-arylpyrroles
    • Pavri, N. P.; Trudell, M. P. An efficient method for the synthesis of 3-arylpyrroles. J. Org. Chem. 1997, 62, 2649-2651.
    • (1997) J. Org. Chem , vol.62 , pp. 2649-2651
    • Pavri, N.P.1    Trudell, M.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.