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

Ying Cheng; Hai-Bo Yang; Bo Liu; Otto Meth-Cohn; David Watkin; Stephen Humphries

doi:10.1055/s-2002-28513

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Synthesis 2002(7): 0906-0910
DOI: 10.1055/s-2002-28513

PAPER

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

Ying Cheng*^a, Hai-Bo Yang^a, Bo Liu^a, Otto Meth-Cohn*^b, David Watkin^c, Stephen Humphries^c
^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

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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

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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, D_x = 1.26 g cm^-3, µ(MoK_α) = 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.