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Volumn 49, Issue 19, 2008, Pages 3181-3184

Synergistic effects of a specific metal template and H-bonds in controlling macrocyclization: a simple, selective, and effective cyclization from N,N-bis(2-hydroxybenzyl)alkylamine derivatives

Author keywords

Azacrown ether; Hydrogen bond; Macrocyclic compound; Metal template

Indexed keywords

1,3 BIS(TOSYLOXY)PROPANE; ALIPHATIC AMINE; ETHER DERIVATIVE; MACROCYCLIC COMPOUND; METAL; N,N BIS(2 HYDROXY 5 ETHYLBENZYL)METHYLAMINE; N,N BIS(2 HYDROXY 5 ETHYLBENZYL)PROPYLAMINE; PROPANE; UNCLASSIFIED DRUG;

EID: 41649109762     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.153     Document Type: Article
Times cited : (7)

References (15)
  • 1
    • 0041437436 scopus 로고    scopus 로고
    • Atwood J.L., and Steed J.W. (Eds), Marcel Dekker, New York
    • Dietrich B. In: Atwood J.L., and Steed J.W. (Eds). Encyclopedia of Supramolecular Chemistry Vol. 1 (2004), Marcel Dekker, New York 830-844
    • (2004) Encyclopedia of Supramolecular Chemistry , vol.1 , pp. 830-844
    • Dietrich, B.1
  • 7
    • 41649098661 scopus 로고    scopus 로고
    • note
    • 15 1 (0.27 g, 1 mmol) was refluxed in acetonitrile (150 mL) with potassium hydroxide (0.11 g, 2 mmol) for 1 h. A solution of 1,3-bis(tosyloxy)propane (0.38 g, 1 mmol) in acetonitrile (70 mL) was added dropwise and the reaction refluxed for 3 days before removing the solvent. The crude product was dissolved in dichloromethane and washed several times with water, before drying over anhydrous sodium sulfate. The solvent was removed to obtain a white solid product in 75% yield.
  • 8
    • 41649107501 scopus 로고    scopus 로고
    • note
    • 2N: C, 77.14; H, 8.09; N, 4.50. Found: C, 76.38; H, 7.69; N, 4.46.
  • 9
    • 41649089540 scopus 로고    scopus 로고
    • note
    • 1H NOESY; H2:H3,H10; H3:H2,H8; H5:H7,H8,H9; H7:H5,H9,H10; H8:H3,H5; H9:H5,H7; H10:H2,H7,H11; H11:H10.
  • 10
    • 41649101850 scopus 로고    scopus 로고
    • note
    • 1 = 0.047 and Rw = 0.121. X-ray data for compound 4b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 258583. Copies of the data may be obtained free of charge from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44-1223-336-033. e-mail: deposit@ccdc.cam.ac.uk).
  • 11
    • 41649121083 scopus 로고    scopus 로고
    • note
    • 6 = 8.20 Hz); MALDI-TOF MS: m/z 338.85.
  • 12
    • 41649095919 scopus 로고    scopus 로고
    • note
    • 7 = 8.20 Hz), 7.07 (s, 2H, Ar-H); MALDI-TOF MS: m/z 340.75.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.