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

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

Abstract

All articles of this category

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

Full Text

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

6a Meth-Cohn O. Taylor DL. J. Chem. Soc., Chem. Commun. 1995, 1463

6b Cheng Y. Meth-Cohn O. Taylor DL. J. Chem. Soc., Perkin Trans. 1 1998, 1257

7 Cheng Y. Liu Q.-X. Meth-Cohn O. Synthesis 2000, 640

8 Cheng Y. Liu Q.-X. Meth-Cohn O. Tetrahedron Lett. 2000, 41: 3475

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.

10 Cheng Y. Ye H.-L. Zhan Y.-H. Meth-Cohn O. Synthesis 2001, 904

11 Sheppard WA. Organic Synthesis, Coll. Vol. 5 Wiley; New York: 1973. p.1085