메뉴 건너뛰기




Volumn , Issue 7, 1999, Pages 1091-1093

A concise route to novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexanes

Author keywords

Azabicyclohexane; Ene carbamate; Intramolecular; Photocycloaddition; 2+2

Indexed keywords

ACETOPHENONE; ALKYL ARYL KETONE; ALLYLAMINE; CARBAMIC ACID DERIVATIVE; CYCLOHEXANE; NICOTINE;

EID: 0032813742     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2775     Document Type: Article
Times cited : (37)

References (30)
  • 5
    • 0000167986 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford, Chapter 2.3
    • (b) Crimmins, M. T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 2.3.
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Crimmins, M.T.1
  • 6
    • 0029920529 scopus 로고    scopus 로고
    • For a new entry into the 2-azabicyclo[2.1.1]hexanes, see: Stevens, C.; De Kimpe, N. J. Org. Chem. 1996, 61, 2174.
    • (1996) J. Org. Chem. , vol.61 , pp. 2174
    • Stevens, C.1    De Kimpe, N.2
  • 13
    • 0345190220 scopus 로고
    • The only other 1-substituted-2-azabicyclo[2.1.1]hexane that has been reported is 1-methyl-2-azabicyclo[2.1.1]hexane, which was prepared from 2,4-methanoproline. See: Davies, J. W.; Malpass, J. R.; Walker, M. P. J. Chem. Soc. Chem. Commun. 1985, 686.
    • (1985) J. Chem. Soc. Chem. Commun. , pp. 686
    • Davies, J.W.1    Malpass, J.R.2    Walker, M.P.3
  • 21
    • 0344070899 scopus 로고    scopus 로고
    • note
    • 2 (265.74): C, 63.28; H, 6.07; N, 5.27. Found: C, 63.29, H, 6.03, N, 5.14.
  • 22
    • 0345364397 scopus 로고    scopus 로고
    • note
    • Significant improvement in isolated yield of 9a (87%) was obtained when distilled ene-carbamate 8a was used.
  • 23
    • 0345364395 scopus 로고    scopus 로고
    • note
    • The estimated purity of ene-carbamates 8i and 8j was only 78% and 70%, respectively, by NMR spectroscopy.
  • 27
    • 0344070895 scopus 로고    scopus 로고
    • note
    • Inter-nitrogen distance for compound 4b ranges from 4.32-4.99 Å based on rotation of the bond connecting the pyridine to the azabicyclic ring.
  • 30
    • 0345364393 scopus 로고    scopus 로고
    • note
    • Compound 4b was shown to activate acetylcholine receptors in embryonic cockroach neuronal cells. This response to application of 4b was blocked by the nAChR antagonist mecamylamine. Thus, 4b appears to be a nAChR agonist.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.