Synthesis of 1,2,2a,3-Tetrahydro-1,4,7b-triazacyclopenta[cd]indenes

Abstract

1,2,2a,3-Tetrahydro-1,4,7b-triazacyclopenta[cd]indenes 12 were obtained from 3-halomethyl-5-chloro-6- or 8-nitropyridines in a novel reaction sequence which comprises a nucleophilic aromatic substitution followed by an intramolecular nucleophilic substitution. The starting material for this reaction (9a) can be prepared in good yields by halocyclization of the easily ­accessible 2-allylamino-6-chloro-3-nitropyridine (4a). Aliphatic as well as aromatic amines are suitable unless they are strongly deactivated. The tricyclic compounds are relatively reactive electrophiles and may serve as interesting intermediates for combinatorial syntheses.

Key words

polycycles - ring closure - nucleophilic aromatic substitutions - halogenation - amines

References

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