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Synthesis of Regioisomeric Pyrido[ c ]azocanones from Azaindanone Derivatives
Author(s) -
Penning Miriam,
Christoffers Jens
Publication year - 2014
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.201301736
Subject(s) - chemistry , diethyl malonate , diketone , moiety , alkylation , methylamine , malonate , ring (chemistry) , stereochemistry , pyridine , medicinal chemistry , condensation reaction , organic chemistry , catalysis
Abstract A ring enlargement reaction with methylamine gave new pyrido[2,3‐ c ]‐, pyrido[3,4‐ c ]‐ and pyrido[3,2‐ c ]azocanone derivatives from cyclic β‐oxo esters with a cyclopentapyridine skeleton and a 1,4‐diketone moiety. The starting materials for this ring transformation were either prepared from halogenopyridine carboxylates by Heck reaction and subsequent hydrogenation, or (halogenomethyl)pyridine carboxylates were submitted to S N reaction with diethyl malonate. Both routes were completed by Dieckmann condensation to build the cyclic β‐oxo ester structure and alkylation with phenacylbromide to install the 1,4‐diketone motif.