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Paper | Regular issue | Vol 78, No. 11, 2009, pp.2799-2809
Published online, 20th August, 2009
DOI: 10.3987/COM-09-11789
Diels-Alder Reactions between Acrolein N,N-Dimethylhydrazone and N-Benzylated Benzotriazole-, Indazole- or Indole-4,7-diones

Christelle Marminon,* Bernard Fenet, Valeria Mignosi, Raphael Terreux, and Pascal Nebois

*INSERM U 863, Laboratory of Organic Chemsitry , University of Lyon 1, ISPB, 8 avenue Rockefeller, 69373 Lyon cedex 08, France

Abstract

Diels-Alder reactions between acrolein N,N-dimethylhydrazone 4 and N-benzylated benzotriazole, indazole and indole-4,7-diones 1, 2 and 3 afforded new heterotricyclic quinones 5, 7 and 9 including from 2 to 4 intracyclic nitrogen atoms. A structural assignment of all new compounds was achieved using 2D NMR 1H-13C HMBC correlations. The single 1,8- regioisomer was isolated starting from benzotriazole or indazole quinones, while a mixture of the 1,5- and 1,8- regioisomers was obtained from an indole-4,7-dione derivative. In all cases, the observed regiochemistry was in agreement with FMO calculation.