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Volumn 71, Issue 18, 2006, Pages 7028-7034

Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSTS; ISOMERIZATION; MOLECULAR DYNAMICS; RUTHENIUM; SYNTHESIS (CHEMICAL);

EID: 33750490398     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061180j     Document Type: Article
Times cited : (71)

References (75)
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  • 3
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    • For recent reviews on the application of RCM to the synthesis of nitrogen heterocycles, see: (a) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693-3712.
    • (2003) Eur. J. Org. Chem. , pp. 3693-3712
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  • 4
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    • Gribble, G. W., Joule, J. A., Eds.; Pergamon: Amsterdam
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    • (2003) Progress in Heterocyclic Chemistry , vol.15 , pp. 1-36
    • Walters, M.A.1
  • 15
    • 0004087670 scopus 로고
    • Rapoport, Z., Ed.; Wiley: New York
    • Rapoport, Z., Ed. The Chemistry of Enamines; Wiley: New York, 1994.
    • (1994) The Chemistry of Enamines
  • 18
    • 14944348646 scopus 로고    scopus 로고
    • For a review, see and references therein
    • For a review, see: Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973-986 and references therein.
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    • Dehli, J.R.1    Legros, J.2    Bolm, C.3
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    • See also ref 13d
    • (d) See also ref 13d.
  • 43
    • 0001678286 scopus 로고
    • For similar tungsten-mediated tandem metathesis-olefination sequences, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3800-3801
    • Fu, G.C.1    Grubbs, R.H.2
  • 44
    • 0000091226 scopus 로고
    • For the pioneering use of the Tebbe reagent to promote the ring-opening metathesis of a strained olefin followed by intramolecular olefination. see: (a) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855-856.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 855-856
    • Stille, J.R.1    Grubbs, R.H.2
  • 47
    • 0037492367 scopus 로고    scopus 로고
    • For recent examples of olefination of tertiary amides with Takeda reagents, see: (a) Takeda, T.; Saito, J.; Tsubouchi, A. Tetrahedron Lett. 2003, 44, 5571-5574.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5571-5574
    • Takeda, T.1    Saito, J.2    Tsubouchi, A.3
  • 57
    • 33750445683 scopus 로고    scopus 로고
    • See also refs 3b and 3d
    • (b) See also refs 3b and 3d.
  • 59
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    • note
    • 9.16
  • 60
    • 33750472777 scopus 로고    scopus 로고
    • note
    • As far as we know, this alkylation is unprecedented. In fact, we have observed that styrene can be converted into 1-propenylbenzene by treatment with dimethyltitanocene (2 molar equiv) in toluene at reflux for 8 h. We appreciate the suggestion of one of the reviewers pointing out a plausible mechanism for this transformation: a [2 + 2] cycloaddition between the titanium carbene and the alkene followed by β-hydride abstraction would give an allyl titanium hydride, which would undergo reductive elimination.
  • 61
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    • note
    • For a preliminary communication of this part of the work, see ref 24.
  • 63
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    • See also ref 3d
    • (b) See also ref 3d.
  • 64
    • 33750476392 scopus 로고    scopus 로고
    • note
    • For an example of 1,2-dihydroisoquinoline synthesis by RCM. see ref 3c.
  • 67
    • 33750440871 scopus 로고    scopus 로고
    • See also ref 3a
    • (c) See also ref 3a.
  • 68
    • 3943048796 scopus 로고    scopus 로고
    • and references therein
    • For a discussion, see: Schmidt, B. Eur. J. Org. Chem. 2004, 1865-1880 and references therein.
    • (2004) Eur. J. Org. Chem. , pp. 1865-1880
    • Schmidt, B.1
  • 69
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    • For reviews of nonmetathetic activities of Grubbs ruthenium catalysts, see: (a) Alcaide, B.; Almendros, P. Chem.-Eur. J. 2003, 9, 1258-1262.
    • (2003) Chem.-Eur. J. , vol.9 , pp. 1258-1262
    • Alcaide, B.1    Almendros, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.