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Volumn , Issue 2, 2008, Pages 233-236

Investigation of the reaction of o-aminonitriles with ketones: A new modification of Friedländer reaction and structures of its products

Author keywords

Cyclizations; Friedl nder reactions; Molecular recognition; Rearrangements; Spiro compounds

Indexed keywords

14 (3 NITROPHENYL) 9,10,11,12 TETRAHYDRO 14H NAPHTHO[1',2':5,6]PYRANO[2,3 B]QUINOLIN 13 AMINE; 2 AMINONITRILE DERIVATIVE; 2,2 BUTAMETHYLENE 6 NITRO 1,2 DIHYDROQUINAZOLIN 4(3H) ONE; 2,3 DIHYDROQUINAZOLIN 4(1H) ONE; 6 CHLORO 2,2 PENTAMETHYLENE 1,2 DIHYDROQUINAZOLIN 4(3H) ONE; 8,9,12 TRIHYDRO 9,9 PENTAMETHYLENE 12 (3 NITROPHENYL) 11H NAPHTHOL[1',2':5,6]PYRANO[2,3 D]PYRIMIDIN 11(10H) ONE; AMINE; CYCLOHEXANONE; KETONE; NITRILE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 38949159951     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000841     Document Type: Article
Times cited : (46)

References (49)
  • 6
    • 38949193389 scopus 로고    scopus 로고
    • Abd El-Wahab, A. H. F. Acta Pharm. 2002, 54, 269.
    • Abd El-Wahab, A. H. F. Acta Pharm. 2002, 54, 269.
  • 11
    • 38949136533 scopus 로고    scopus 로고
    • Grubs, G. S.; Zhi, L.; Jones, T. K.; Marschke, K. B.; Tegley, C. M. PCT Int. Appl., WO0066560, 2000.
    • (b) Grubs, G. S.; Zhi, L.; Jones, T. K.; Marschke, K. B.; Tegley, C. M. PCT Int. Appl., WO0066560, 2000.
  • 14
    • 38949156994 scopus 로고    scopus 로고
    • Chem. Abstr. 2002, 138, 256866j.
    • (2002) Chem. Abstr , vol.138
  • 15
    • 38949192720 scopus 로고    scopus 로고
    • Patent, JP200491403
    • (c) Yoshida, T. Jpn. Patent, JP200491403, 2004.
    • (2004)
    • Yoshida, T.J.1
  • 37
    • 23744474232 scopus 로고    scopus 로고
    • Haviv, H. R.; Wong, D. M.; G reenblatt, H. M.; Carlier, P. R.; Han, Y. F.; Pang, Y. P.; Silman, I.; Sussman, J. L. J. Am. Chem. Soc. 2005, 127, 11029.
    • (d) Haviv, H. R.; Wong, D. M.; G reenblatt, H. M.; Carlier, P. R.; Han, Y. F.; Pang, Y. P.; Silman, I.; Sussman, J. L. J. Am. Chem. Soc. 2005, 127, 11029.
  • 41
    • 38949141771 scopus 로고    scopus 로고
    • Typical Procedure for Preparation of Products 2 and 4: o-Aminonitrile 1 (1.5 mmol, cyclohexanone (1.7 mmol, anhyd zinc chloride (1.6 mmol) and DMF (10 mL) were added into a 50-mL flask. The reaction mixture was refluxed for 2 h (monitored by TLC, Then the mixture was diluted with H2O and titrated to pH 12-13 by 20% NaOH. After filtration, the solid was dissolved in THF, the organic phase obtained was combined with the extracted component of filtrate (using EtOAc) and evaporated in vacuo, and then chromatographed (Merck, 200-300 mesh, EtOAc-PE, 1:2) to afford product 2 and 4. Selected data for compounds 2, 4 and 8: 14-(3-Nitrophenyl)-9,10,11,12-tetrahydro-14H-naphtho[1′, 2′:5,6]pyrano[2,3-b]quinolin-13-amine (2a, yellow solid; mp 287-289°C. IR (KBr, 3450, 3364, 2935, 1640, 1607, 1573, 1523, 1445, 1348, 1232 cm-1. 1H NMR: 400 MHz, CDCl 3
    • 3: C, 58.29; H, 5.30; N, 16.99. Found: C, 58.33; H, 5.31; N, 17.08.
  • 45
    • 38949119585 scopus 로고    scopus 로고
    • CCDC 660416 (4a) and CCDC 667600(4b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
    • CCDC 660416 (4a) and CCDC 667600(4b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
  • 49
    • 38949158610 scopus 로고    scopus 로고
    • This new conversion is abbreviated as PDF conversion, which means a new conversion from Pinner to Dimroth rearrangement in the Friedländer reaction
    • This new conversion is abbreviated as PDF conversion, which means a new conversion from Pinner to Dimroth rearrangement in the Friedländer reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.