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Attempts to prepare some 3‐substituted azolo[1,2‐ x ]azines, intermediates in the synthesis of azaaplysinopsin derivatives
Author(s) -
Jukić Lucija,
Čopar Anton,
Stanovnik Branko,
Svete Jurij,
Malešič Mateja,
Krbavčič Aleš
Publication year - 1999
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.5570360506
Subject(s) - chemistry , pyrazine , bicyclic molecule , nitrile , pyridine , dimethylformamide , acetal , oxazolone , medicinal chemistry , organic chemistry , solvent
Some 3‐substituted pyrrolo[1,2‐ a ]azines 4a‐d were prepared in low yields from the corresponding 2‐methylpyridines 1a,b and pyrazine derivatives 1c,d by quaternization with methyl bromoacetate followed by treatment with N,N ‐dimethylformamide dimethyl acetal. Ethyl 2‐pyridinylacetate ( 5 ) and 2‐pyridinylaceto‐nitrile ( 6 ) were converted with 4‐(2‐bromo‐1‐dimethylaminoethylidene)‐2‐phenyl‐5(4 H )‐oxazolone ( 9 ) into pyrrolo[1,2‐ a ]pyridine derivatives 10 and 12 , intermediates in the synthesis of azaaplysinopsins.