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Reaction of malonates with camphoranile synthesis of 4‐hydroxy‐2‐pyridones attached to the bornane ring system
Author(s) -
Kafka Stanislav,
Aigner Rudolf,
Kappe Thomas
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430444
Subject(s) - chemistry , malonate , diethyl malonate , derivative (finance) , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
The reaction of camphoraniles 3a,b with “magic malonates” (bis‐2,4,6‐trichlorophenylmalonates) 4a,b leads to 4‐hydroxy‐2(1 H )‐pyridones attached to bornane ring system 6a‐c in good yields. Less satisfactory yields were obtained with the diethyl malonate 5b . The reaction of an excess of diethyl malonate 5 itself with 3b yields the pyrono derivative 7 , which can readily be degraded via the acetyl derivative 8 to the basic structure 9 .