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Volumn , Issue 7, 2004, Pages 1444-1454

Synthesis of polyfluorinated nitrogen-containing heterocycles from hemifluorinated enones or organofluorosilicon building blocks as synthetic equivalents

Author keywords

Acylsilanes; Michael addition; Nitrogen heterocycles; Organofluorine; Silyl enol ethers

Indexed keywords

2 (1' FLUORO 2' OXO 2' HEPTYL) 2 (PERFLUOROBUTYL) 1 OXAZOLIDINE; 2 (1' FLUORO 2' OXO 2' PHENYLETHYL) 1 METHYL 2 (PERFLUOROBUTYL) 1 OXAZOLIDINE; 2 (1' FLUORO 2' OXO 2' PHENYLETHYL) 1 METHYL 2 (PERFLUOROBUTYL) IMIDAZOLIDINE; 2 (1' FLUORO 2' OXO 2' PHENYLETHYL) 2 (PERFLUOROBUTYL) 1 OXAZOLIDINE; 2 (1' FLUORO 2' OXO 2' PHENYLETHYL) 2 PERFLUOROBUTYLIMIDAZOLIDINE; 2 AMINO 6 (1' DEOXY 2',3':4',5' DI O ISOPROPYLIDENE DEXTRO XYLITYL) 5 FLUORO 4 (PERFLUOROETHYL)PYRIMIDINE; 3 FLUORO 2 (4' FLUOROPHENYL) 4 (PERFLUOROBUTYL)QUINOLINE; 3 FLUORO 2 (PERFLUOROBUTYL) 4 PHENYLBENZO 1,5 DIAZEPINE; 3 FLUORO 4 (4' FLUOROPHENYL) 2 (PERFLUOROBUTYL)BENZO 1,5 THIAZEPINE; 3 FLUORO 4 (4' FLUOROPHENYL)BENZO 1,5 DIAZEPINE; 3 FLUORO 4 (4' METHOXYPHENYL) 2 (PERFLUOROBUTYL)BENZO 1,5 DIAZEPINE; 3 FLUORO 4 PENTYL 2 (PERFLUOROBUTYL)BENZO 1,5 DIAZEPINE; 4 (1' DEOXY 2',3':4',5' DI O ISOPROPYLIDENE DEXTRO XYLITYL) 3 FLUORO 2 (PERFLUOROETHYL)BENZO 1,5 DIAZEPINE; 4 (1' DEOXY 2',3':4',5' DI O ISOPROPYLIDENE DEXTRO XYLITYL) 3 FLUORO 2 (PERFLUOROETHYL)BENZO 1,5 THIAZEPINE; 4 (3' O BENZYL 5' DEOXY 1',2' O ISOPROPYLIDENE ALPHA DEXTRO XYLOFURANOSYL) 3 FLUORO 2 (PERFLUOROETHYL)BENZO 1,5 DIAZEPINE; 4 (4' CHLOROPHENYL) 3 FLUORO 2 (PERFLUOROBUTYL)BENZO 1,5 DIAZEPINE; 4 [3' O BENZYL 5' (1',2' O ISOPROPYLIDENE) ALPHA DEXTRO XYLOFURANOSYL] 3 FLUORO 2 (PERFLUOROETHYL)BENZO 1,5 THIAZEPINE; 5 FLUORO 6 (4' FLUOROPHENYL) 4 (PERFLUOROBUTYL)PYRIMIDINE; 6 (1' DEOXY 2',3':4',5' DI O ISOPROPYLIDENE DEXTRO XYLITYL) 5 FLUORO 2 METHOXY 4 (PERFLUOROETHYL)PYRIMIDINE; 6 (1' DEOXY 2',3':4',5' DI O ISOPROPYLIDENE DEXTRO XYLITYL) 5 FLUORO 2 METHYL 4 (PERFLUOROETHYL)PYRIMIDINE; 6 (1' DEOXY 2',3':4',5' DI O ISOPROPYLIDENE DEXTRO XYLITYL) 5 FLUORO 4 (PERFLUOROETHYL)PYRIMIDINE; BENZODIAZEPINE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLINE DERIVATIVE; NITROGEN DERIVATIVE; OXAZOLIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 4544384113     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300671     Document Type: Article
Times cited : (20)

References (49)
  • 2
    • 0023237559 scopus 로고
    • [1b] J. T. Welch, Tetrahedron 1987, 43, 3123-3197.
    • (1987) Tetrahedron , vol.43 , pp. 3123-3197
    • Welch, J.T.1
  • 4
    • 0003518240 scopus 로고    scopus 로고
    • (Eds. I. Ojima, J. R. McCarthy, J. T. Welch); A.C.S. Editions, Washington, DC
    • [2a] Biomedical Frontiers of Fluorine Chemistry (Eds. I. Ojima, J. R. McCarthy, J. T. Welch); A.C.S. Editions, Washington, DC, 1996.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
  • 7
    • 0004039074 scopus 로고
    • (Eds.: T. Eicher, S. Hauptmann), Georg Thieme Verlag, Stuttgart
    • The Chemistry of Heterocycles. (Eds.: T. Eicher, S. Hauptmann), Georg Thieme Verlag, Stuttgart, 1995. Comprehensive Heterocyclic Chemistry II. (Eds.: A.R. Katritzky, C. W. Rees, E. F. V. Scriven), Elsevier, Oxford, UK, 1996.
    • (1995) The Chemistry of Heterocycles
  • 8
    • 0003607021 scopus 로고    scopus 로고
    • (Eds.: A.R. Katritzky, C. W. Rees, E. F. V. Scriven), Elsevier, Oxford, UK
    • The Chemistry of Heterocycles. (Eds.: T. Eicher, S. Hauptmann), Georg Thieme Verlag, Stuttgart, 1995. Comprehensive Heterocyclic Chemistry II. (Eds.: A.R. Katritzky, C. W. Rees, E. F. V. Scriven), Elsevier, Oxford, UK, 1996.
    • (1996) Comprehensive Heterocyclic Chemistry II
  • 14
    • 0034703491 scopus 로고    scopus 로고
    • [5b] For trifluoromethylation, see: R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632. M. A. McClinton, D. A. McClinton, Tetrahedron 1992, 48, 6555-6666.
    • (2000) Tetrahedron , vol.56 , pp. 7613-7632
    • Singh, R.P.1    Shreeve, J.M.2
  • 15
    • 0026760246 scopus 로고
    • [5b] For trifluoromethylation, see: R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632. M. A. McClinton, D. A. McClinton, Tetrahedron 1992, 48, 6555-6666.
    • (1992) Tetrahedron , vol.48 , pp. 6555-6666
    • McClinton, M.A.1    McClinton, D.A.2
  • 16
    • 0031140114 scopus 로고    scopus 로고
    • [5c] For perfluoroalkylation, see: G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786. D. J. Burton, Z.-I. Yang, Tetrahedron 1992, 48, 189-275.
    • (1997) Chem. Rev. , vol.97 , pp. 757-786
    • Prakash, G.K.S.1    Yudin, A.K.2
  • 17
    • 0026501144 scopus 로고
    • [5c] For perfluoroalkylation, see: G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786. D. J. Burton, Z.-I. Yang, Tetrahedron 1992, 48, 189-275.
    • (1992) Tetrahedron , vol.48 , pp. 189-275
    • Burton, D.J.1    Yang, Z.-I.2
  • 43
    • 4544281687 scopus 로고    scopus 로고
    • note
    • The α-hydroperfluoro ketone is itself a synthetic equivalent of the corresponding enone. Under the conditions used in the synthesis of the heterocycles, it easily loses hydrogen fluoride and is finally converted into the heterocycle. Hence, the heterocycle synthesis could have been directly performed on the ketone/enone mixture, as we have observed in further applications (see ref [28])


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.