Synthesis 2005(18): 3107-3118  
DOI: 10.1055/s-2005-918409
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Sylvia Schmid, Daniel Schühle, Simon Steinberger, Zhang Xin, Volkhard Austel*
Abteilung Organische Chemie II, Universität Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
e-Mail: volkhard.austel@chemie.uni-ulm.de;
Further Information

Publication History

Received 13 May 2005
Publication Date:
29 September 2005 (online)

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.

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