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

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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

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References

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