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Synlett 2010(14): 2109-2113  
DOI: 10.1055/s-0030-1258536
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

tert-Amino Effect in peri-Substituted Naphthalenes: Syntheses of Naphthazepine and Naphthazonine Ring Systems

Ágota Anna Földia, Krisztina Ludányib, Attila Csaba Bényeic, Péter Mátyus*a
a Department of Organic Chemistry, Semmelweis University, Hőgyes Endre utca 7., 1092 Budapest, Hungary
Fax: +36(1)2170851; e-Mail: peter.matyus@szerves.sote.hu;
b Department of Pharmacy, Semmelweis University, Hőgyes Endre utca 7., 1092 Budapest, Hungary
c Department of Chemistry, Laboratory for X-ray Diffraction, University of Debrecen, Egyetem tér 1., 4010 Debrecen, Hungary
Further Information

Publication History

Received 20 May 2010
Publication Date:
30 July 2010 (online)

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Abstract

Novel straightforward syntheses of naphtho-fused azepines and benzazonine via tert-amino effect are described. Starting from 1-naphthylamine, 8-N,N-dialkylaminonaphthalene-1-carb­aldehydes could be obtained in two steps. The aldehyde was prepared by a Suzuki reaction of 8-bromonaphthalene-1-carbaldehyde with ortho-pyrrolidinophenylboronic acid. Treatment of aldehydes with active methylene compounds afforded naphthazepines and novel benzazonine ring system, respectively, through rearrangement of isolable vinyl intermediates or benzo[de]quinolinium derivatives or without isolation of any intermediates. A mechanistic investigation supports an intramolecular hydride transfer for the ring closure to azepine or azonine. Our results indicate that the tert-amino effect may provide a valuable approach to the synthesis of ortho- and peri-fused aza-ring systems.

Key words

tert-amino effect - naphthazepine - naphthazonine - benzo[d,e]quinolinium - peri-interaction

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The X-ray data are available from the Cambridge Crystallographic Data Centre CCDC under the numbers 5: 7770044, 7: 777045, 10: 777046, 11: 777047, 15: 777048, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk. The details of the X-ray structures will be published elsewhere.

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Experimental data are available in Supporting Information.