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Rearrangements of 5‐acetyl‐3‐benzoylamino‐6‐(2‐dimethylamino‐1‐ethenyl)‐2 H ‐pyran‐2‐one and 3‐benzoylamino‐6‐(2‐dimethylamino‐1‐ethenyl)‐5‐ethoxycarbonyl‐2 H ‐pyran‐2‐one into 1‐aminopyridine, pyrano[2,3‐ b ]pyridine and isoxazole derivatives
Author(s) -
Strah Sonja,
Svete Jurij,
Stanovnik Branko
Publication year - 1996
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.5570330449
Subject(s) - chemistry , hydroxylamine , nucleophile , isoxazole , pyran , hydrazine (antidepressant) , pyridine , medicinal chemistry , ammonia , organic chemistry , catalysis , chromatography
Rearrangements of 5‐acetyl‐3‐benzoylamino‐6‐(2‐dimethylamino‐1‐ethenyl)‐2 H ‐pyran‐2‐one ( 1 ) and 3‐benzoylamino‐6‐(2‐dimethylamino‐1‐ethenyl)‐5‐ethoxycarbonyl‐2 H ‐pyran‐2‐one ( 7 ) in the presence of N ‐nucleophiles, such as ammonia, hydrazine, and hydroxylamine, into 1‐aminopyridine, pyrano[2,3‐ b ]‐pyridine, and isoxazole derivatives 5, 11 , and 15 is described. In the reaction of compounds 1 and 7 with C‐nucleophiles, such as 5,5‐dimethyl‐1,3‐cyclohexanedione and barbituric acid, only substitution of the dimethylamino group is taking place to give the compounds 17, 18 , and 20 .