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Synthesis 2002(7): 0906-0910
DOI: 10.1055/s-2002-28513
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Very Simple Route to Benzonaphtho[1,5]Diazocines Using Vilsmeier Reagents via the ‘t-Amino Effect’

Ying Cheng*a, Hai-Bo Yanga, Bo Liua, Otto Meth-Cohn*b, David Watkinc, Stephen Humphriesc
a Department of Chemistry, Beijing Normal University, Beijing 100875, China
e-Mail: yincheng@95777.com;
b Chemistry Department, Sunderland University, Sunderland, UK SR1 3SD, UK
e-Mail: otto.meth-cohn@sunderland.ac.uk ;
c Chemical Crystallography, University of Oxford, Oxford, OX1 3PD, UK
Further Information

Publication History

Received 5 March 2002
Publication Date:
14 May 2002 (online)

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Abstract

The novel fused heterocyclic systems 7,8,13,14-tetrahydrobenzo[b]naphtho[1,2-f][1,5]diazocine and 7,8,13,14-tetrahydrobenzo[b]naphtho[2,1-f][1,5]diazocine were prepared in moderate yields in a one step reaction by Vilsmeier formylation of 1-dimethyl-aminonaphthalene or 2-dimethylaminonaphthalene, respectively, by way of the ‘t-amino effect’. Novel rearranged by-products were formed from 2-dimethylaminonaphthalene.

Key words

Vilsmeier - dimethylaminonaphthalenes - benzonaphthodiazocines

    References

  • 1 Cooper FC. Partridge MW. J. Chem. Soc.  1955,  991 
  • 2a Roy RB. Swan GA. J. Chem. Soc., Chem. Commun.  1966,  427 
  • 2b Swan GA. J. Chem. Soc., Chem. Commun.  1968,  1376 
  • 3a Sakakibara T. Matsuyama H. Chem. Lett.  1980,  1331 
  • 3b Sakakibara T. Matsuyama H. Chem. Lett.  1982,  1823 
  • 4a Farrar WV. Chem. Ind. (London)  1967,  1644 
  • 4b Demir T. Shaw RA. Chem. Ind. (London)  1976,  112 
  • 5 Demir T. Shaw RA. J. Chem. Soc., Perkin Trans. 1  1987,  1547 
    Crossref
  • 6a Meth-Cohn O. Taylor DL. J. Chem. Soc., Chem. Commun.  1995,  1463 
    Crossref
  • 6b Cheng Y. Meth-Cohn O. Taylor DL. J. Chem. Soc., Perkin Trans. 1  1998,  1257 
    Crossref
  • 7 Cheng Y. Liu Q.-X. Meth-Cohn O. Synthesis  2000,  640 
    Thieme Connect
  • 8 Cheng Y. Liu Q.-X. Meth-Cohn O. Tetrahedron Lett.  2000,  41:  3475 
    CrossrefSearch in Google Scholar
  • 10 Cheng Y. Ye H.-L. Zhan Y.-H. Meth-Cohn O. Synthesis  2001,  904 
    Thieme Connect
  • 11 Sheppard WA. Organic Synthesis, Coll. Vol. 5   Wiley; New York: 1973.  p.1085 
9

Crystal data for 14 (X = F): C19N2H19F, M = 294.37, monoclinic, space group P121/c1, a = 10.1403(2), b = 11.2671(2), c = 14.0685(3) Å, β = 105.880(1)o, V = 1546.0 Å3, Z = 4, Dx = 1.26 g cm-3, µ(MoKα) = 0.71073 Å, T = 190 K; colourless blocks, 0.20Î0.20Î0.30 mm, Enraf-Nonius Kappa CCD diffractometer, ω-scans, 3507 independent reflections. The structure was solved using the direct-methods program SIR922, which located all non-hydrogen atoms. Subsequent full-matrix least-squares refinement was carried out using the CRYSTALS3 program suite. Coordinates and anisotropic thermal parameters of all non-hydrogen atoms were refined. Hydrogen atoms were located in a difference Fourier map but placed at geometrically calculated positions. Refinement converged satisfactorily to give R = 0.042, wR = 0.059. CCDC reference number 180234.