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A New and Efficient Synthesis of Derivatives of Octahydro‐4 H ‐pyrrolo[1,2‐ c ]pyrido[1′,2′‐ a ]imidazole
Author(s) -
Rouchaud Anne,
Braekman JeanClaude
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001704
Subject(s) - chemistry , imidazole , decarboxylation , substituent , malonate , oxidative decarboxylation , stereochemistry , n bromosuccinimide , diethyl malonate , tricyclic , medicinal chemistry , halogenation , organic chemistry , catalysis , enzyme
When diethyl malonate was added to a solution of Δ 1 ‐piperideine, generated in situ by oxidative desamination and decarboxylation of L ‐lysine by N ‐bromosuccinimide (NBS), formation of the unexpected tricyclic compound 6 (4‐diethylmalonyl‐octahydro‐4 H ‐pyrrolo[1,2‐ c ]pyrido[1′,2′‐ a ]imidazole)was observed. The structure of 6 was deduced from analysis of its spectroscopic data and was confirmed both by chemical degradation and by total synthesis. We proved that 3‐bromo‐1‐piperideine was implicated in its formation. Moreover, based on this feature, a new and efficient synthesis of 6 was developed. The elaborated pathway was adapted to access derivatives related to 6 that differed in their C‐4 substituent.