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Synthesis of herbicidal 3‐substituted‐4(3 H )‐pyrimidinones under high pressure
Author(s) -
Jezewski Artur,
Jurczak Janusz,
Lidert Zev,
Tice Colin M.
Publication year - 2001
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.5570380316
Subject(s) - chemistry , pyrimidinones , yield (engineering) , amidine , medicinal chemistry , high pressure , scope (computer science) , organic chemistry , combinatorial chemistry , computer science , programming language , materials science , engineering physics , engineering , metallurgy
The reaction of an N ‐monosubstituted amidine with a β‐ketoester to afford a pyrimidinone is sluggish at best under normal conditions. We now report that this reaction can be effected in moderate yield under high pressure. Thus, 2,6‐dichloro‐4‐pyridyl‐( N ‐prop‐2‐ynyl)carboxamidine (4b) was reacted with three α‐substituted‐β‐ketoesters (2b‐d) at 10–16 kbar to afford herbicidal 2‐(2,6‐dichloro‐4‐pyridyl)‐3‐(prop‐2‐ynyl)‐4(3 H )‐pyrimidinones 5b and 5c in 15 ‐ 43% yield. This result expands the scope of reactions promoted by application of high pressure.