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Volumn 44, Issue 32, 2005, Pages 5130-5133

Approach to the blues: A highly flexible route to the azulenes

Author keywords

Aromatic compounds; Azulenes; Cycloaddition; Natural products; Synthesis design

Indexed keywords

ADDITION REACTIONS; DECHLORINATION; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 23944514264     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501276     Document Type: Article
Times cited : (46)

References (45)
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    • see, also: H.-J. Hansen, Chimia 1996, 50, 489-496.
    • (1996) Chimia , vol.50 , pp. 489-496
    • Hansen, H.-J.1
  • 4
    • 33947458314 scopus 로고
    • For reviews on the azulenes, see: a) M. Gordon, Chem. Rev. 1952, 52, 127-200;
    • (1952) Chem. Rev. , vol.52 , pp. 127-200
    • Gordon, M.1
  • 8
    • 33645400198 scopus 로고    scopus 로고
    • PhD Thesis, University of Grenoble
    • a) Y. Coquerel, PhD Thesis, University of Grenoble, 2001;
    • (2001)
    • Coquerel, Y.1
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    • 33645412394 scopus 로고    scopus 로고
    • (Kotobuki Seiyaku Co. Ltd., Japan), JP2000007611, 2000
    • T. Toyama, I. Toyama, M. Yokota (Kotobuki Seiyaku Co. Ltd., Japan), JP2000007611, 2000 [Chem. Abstr. 2000, 132, 64 075e];
    • (2000) Chem. Abstr. , vol.132
    • Toyama, T.1    Toyama, I.2    Yokota, M.3
  • 23
    • 33645391336 scopus 로고    scopus 로고
    • note
    • 3, Pd/C; p-chloranil, Δ; HCl, Δ; Martin sulfurane reagent, were not fruitful.
  • 27
    • 3042654141 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 1871-1876.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1871-1876
  • 29
    • 0000491823 scopus 로고
    • b) 1,4-dimethylazulene is naturally occurring, see: D. Meuche, S. Huneck, Chem. Ber. 1966, 99, 2669-2674;
    • (1966) Chem. Ber. , vol.99 , pp. 2669-2674
    • Meuche, D.1    Huneck, S.2
  • 32
    • 33645405111 scopus 로고    scopus 로고
    • note
    • It should be noted that the aromatization of the azulenes, not unexpectedly, is directly dependent on the degree of unsaturation in the substrates; see reference [3b].
  • 33
    • 0003600722 scopus 로고
    • Academic Press, New York
    • Chamazulene is an artifact from various sesquiterpene oils; 7-isopropyl-4-methylazulene and guaiazulene are found naturally in different sources, see: a) T. K. Devon, A. I. Scott in Handbook of Naturally Occurring Compounds, Vol. 2, Academic Press, New York, 1972;
    • (1972) Handbook of Naturally Occurring Compounds , vol.2
    • Devon, T.K.1    Scott, A.I.2
  • 34
    • 0004205843 scopus 로고
    • Chapman and Hall, New York, and references therein
    • b) Dictionary of Terpenoids, Vol. 2 (Eds.: J. D. Connolly, R. A. Hill), Chapman and Hall, New York, 1991, and references therein.
    • (1991) Dictionary of Terpenoids , vol.2
    • Connolly, J.D.1    Hill, R.A.2
  • 38
  • 39
    • 33645410992 scopus 로고    scopus 로고
    • Robugen GmbH Pharmazeutische Fabrik Esslingen A.N. , Germany DE 10065683, 2001
    • an earlier synthesis has been reported in a patent, see: Robugen GmbH Pharmazeutische Fabrik Esslingen A.N. , Germany DE 10065683, 2001 [Chem. Abstr. 2001, 135, 76 647t].
    • (2001) Chem. Abstr. , vol.135
  • 40
    • 33645406340 scopus 로고    scopus 로고
    • note
    • 2;
  • 41
    • 33645393014 scopus 로고    scopus 로고
    • note
    • 3, the Burgess reagent, and p-chloranil;
  • 42
    • 33645404169 scopus 로고    scopus 로고
    • note
    • c) obtained from 7-phenylcycloheptatriene; see references [4a,5];
  • 43
    • 33645387986 scopus 로고    scopus 로고
    • note
    • d) prepared from 6b by using phenylboronic acid rather than methylboronic acid (98 % yield);
  • 44
    • 33645383316 scopus 로고    scopus 로고
    • note
    • 2O and Pd/C in toluene (50 % yield), for several related examples, see reference [4a];


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.