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Synthesis 2010(8): 1291-1302  
DOI: 10.1055/s-0029-1218674
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple and Practical Approach to the Dibenzo[c,f]thiazolo[3,2-a]azepines: A Novel Fused Tetracyclic Azepine System

Alirio Palma*a, Nelson Galeanoa, Ali Bahsasb
a Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia
Fax: +57(76)349069; e-Mail: apalma@uis.edu.co;
b Laboratorio de RMN, Grupo de Productos Naturales, Departamento de Química, Universidad de los Andes, Mérida 5101, Venezuela
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Publication History

Received 7 September 2009
Publication Date:
11 February 2010 (online)

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Abstract

A novel set of functionalized dibenzo[c,f]thiazolo[3,2-a]azepines, which is a new ring system, were successfully synthesized in a four-step protocol starting from readily available substituted N-allyl-N-benzylanilines. The synthesis of the title compounds was accomplished through cyclocondensation of morphanthridines with mercaptoacetic acid. Morphanthridines were prepared by selective oxidation of dihydromorphanthridines with pyridinium chlorochromate in dichloromethane. The dihydromorphanthridines were obtained by acid-catalyzed intramolecular Friedel-Crafts alkylation of substituted 2-allyl-N-benzylanilines, which in turn, were prepared from N-allyl-N-benzylanilines by aromatic amino-Claisen rearrangement. The structural elucidation of all synthesized compounds by high resolution NMR is also reported.

Key words

amino-Claisen rearrangement - intramolecular Friedel-Crafts alkylation - 2-allyl-N-benzylanilines - dihydromorphanthridines - dibenzo[c,f]thiazolo[3,2-a]azepines

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