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CONSTRUCTION OF TETRACYCLIC INDOLE BASES VIA AZA-DIELS-ALDER REACTION OF INDOLYLETHYLIMINES WITH BRASSARD DIENE

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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LOCK, R., & Waldmann, H. (1994). CONSTRUCTION OF TETRACYCLIC INDOLE BASES VIA AZA-DIELS-ALDER REACTION OF INDOLYLETHYLIMINES WITH BRASSARD DIENE. LIEBIGS ANNALEN DER CHEMIE, (5), 511-516.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-72A8-9
Abstract
Schiff's bases 3 derived from tryptamine react with Brassard's diene 4 in the presence of EtAlCl2 to give functionalized 1,2,5,6-tetrahydropyridines which are subsequently transformed to indolo[2,3-a]quinolizines 8-10 by the Bischler-Napieralski reaction and reduction of the intermediate iminium salts with NaBH4.