1. Enaminone-Based Synthesis of Dipodazine Derivatives
- Author
-
Branko Stanovnik, Jernej Wagger, Anton Meden, Jurij Svete, and David Bevk
- Subjects
Inorganic Chemistry ,Chemistry ,Stereochemistry ,Yield (chemistry) ,Organic Chemistry ,Drug Discovery ,Dipodazine ,Physical and Theoretical Chemistry ,Ester hydrochloride ,Biochemistry ,Racemization ,Catalysis - Abstract
A series of racemic dipodazine analogues 9 were prepared in 22–80% yield from (3Z,6RS)-3-[(dimethylamino)methylidene]-6-methyl-1-(phenylmethyl)piperazine-2,5-dione (7) (Scheme 1), which was prepared in four steps from (RS)-alanine methyl ester hydrochloride. The preparation of nonracemic 7 from (S)-alanine methyl ester hydrochloride failed, since the introduction of the enamino functionality at position 3 of the precursor 6 was accompanied by almost complete racemization.
- Published
- 2006
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