Enaminone-Based Synthesis of Dipodazine Derivatives

✍ Scribed by Jernej Wagger; David Bevk; Anton Meden; Jurij Svete; Branko Stanovnik

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 111 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690026

✦ Synopsis

Abstract

A series of racemic dipodazine analogues 9 were prepared in 22–80% yield from (3__Z__,6__RS__)‐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.