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Nitrogen bridgehead compounds. Part 19 . Synthesis of polymethylenepyrimidin‐4‐ones
Author(s) -
Kökösi József,
Szász György,
Hermecz István,
Mészáros Zoltán,
CsákváriPongor Marianne,
Tóth Gábor
Publication year - 1982
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.5570190439
Subject(s) - chemistry , methylene , nuclear magnetic resonance spectroscopy , pyrimidinones , spectroscopy , deuterium , nitrogen , medicinal chemistry , stereochemistry , organic chemistry , physics , quantum mechanics
Reaction of five‐, six‐, seven‐, and eight‐membered cyclic amidines ( 1 n = 0‐3) with diethyl ethoxy‐methylenemalonate ( 2 ) yields isomeric 2,3‐polymethylene‐4(3 H ]‐ and 1,2‐polymethytlene‐4(1 H )‐pyrimidinones ( 3 and 4 ) respectively, n = 0‐3). With 2‐aminopyrroline the isomer ratio was dependent upon the reaction conditions. The structure of the isomers 3 and 4 was studied by uv, ir and 1 H‐nmr spectroscopy. Both isomers contain an active methylene group which can be deuterated. Deuteration was investigated with 1 H‐nmr spectroscopy.