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The synthesis of 3‐[(dimethylamino)(2‐phenyl‐5‐oxo‐2‐oxazolinyl‐idene‐4)methyl]imidazo[1,2‐ x ]azines and related compounds, intermediates in the formation of azaaplysinopsin derivatives
Author(s) -
Bratušek Urška,
Hvala Aleš,
Stanovnik Branko
Publication year - 1998
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.5570350431
Subject(s) - chemistry , sodium methoxide , oxazolone , methanol , medicinal chemistry , conjugated system , ring (chemistry) , imidazole , stereochemistry , organic chemistry , polymer
4‐(2‐Bromo‐1‐dimethylaminoethylidene)‐2‐phenyl‐5(4 H )‐oxazolone ( 5 ) reacts with N,N ‐dimethyl‐ N'‐ heteroarylformamidines 7 to form imidazoazine derivatives 9 with the oxazolone ring connected through a conjugated double bond to the fused imidazole system at position 3. Compounds 9 were transformed with sodium methoxide in methanol into 2‐benzoylamino‐3‐dimethylamino‐3‐imidazoazinylpropenoates 10 , while by treatment with hydrochloric acid in methanol, 3‐(benzoylaminoacetyl)imidazoazines 12 were formed. The synthesis of compounds 9 represents a facile route to intermediates in the synthesis of azaaplysinopsin and related systems.