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Volumn 6, Issue 17, 2004, Pages 3009-3012

Diversity-oriented synthesis of azaspirocycles

Author keywords

[No Author keywords available]

Indexed keywords

5 AZASPIRO[2.4]HEPTANE DERIVATIVE; 5 AZASPIRO[2.5]OCTANE; 5 AZASPIRO[2.6]NONANE DERIVATIVE; ALKYNE DERIVATIVE; AMINE; AZEPINE DERIVATIVE; DICYCLOPROPYLMETHYLAMINE DERIVATIVE; HEPTANE DERIVATIVE; METHYL IODIDE; METHYLENE IODIDE; N DIPHENYLPHOSPHINOYLIMINE DERIVATIVE; NONANOIC ACID; OCTANE; PHOSPHINIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONOCENE;

EID: 4444303072     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0487783     Document Type: Article
Times cited : (52)

References (35)
  • 17
    • 0037428001 scopus 로고    scopus 로고
    • For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
    • (2003) J. Org. Chem. , vol.68 , pp. 62
    • Hoffmann, T.1    Waibel, R.2    Gmeiner, P.3
  • 18
    • 0037132647 scopus 로고    scopus 로고
    • For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14848
    • Wipf, P.1    Rector, S.R.2    Takahashi, H.3
  • 19
    • 0035914638 scopus 로고    scopus 로고
    • For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
    • (2001) Chem. Eur. J. , vol.7 , pp. 4811
    • Furstner, A.1    Guth, O.2    Duffels, A.3    Seidel, G.4    Liebl, M.5    Gabor, B.6    Mynott, R.7
  • 20
    • 0000587503 scopus 로고
    • For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7324
    • Fu, G.C.1    Grubbs, R.H.2
  • 25
    • 4444272441 scopus 로고    scopus 로고
    • note
    • Exposure of A to the allylation conditions led to carbamate cleavage product B, which upon ring-closing metathesis provided the 11-membered C rather than the azepine product. Interestingly, this reaction was much faster (< 1 h) than the formation of azepines 9. (Equation Presented)
  • 29
    • 4444311451 scopus 로고    scopus 로고
    • note
    • These observations are in agreement with the results of Rudolph et al. (ref 17); however, Lewis acidic conditions appear to promote N-dephosphinoylation and do not furnish the desired pyrrolidines in acceptable yields.
  • 34
    • 4444354869 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 23 was assigned by NOESY and the product was assumed to arise from an inversion of configuration at the quaternary carbon atom. (Equation Presented)
  • 35
    • 4444292999 scopus 로고    scopus 로고
    • note
    • Preliminary screening of compounds 3 revealed interesting nuclear receptor binding and antiproliferative effects.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.