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Condensation reactions of 3‐Amino‐4‐imino‐4 H ‐thieno‐[3,4‐ c ][1]benzopyran
Author(s) -
NyiondiBonguen E.,
Sopbué Fondjo E.,
Fomum Z. Tanee,
Döpp Dietrich
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.5570330212
Subject(s) - chemistry , derivative (finance) , yield (engineering) , acylation , trifluoroacetic anhydride , diethyl malonate , hydrolysis , medicinal chemistry , coumarin , aqueous solution , alkali metal , alkaline hydrolysis , organic chemistry , materials science , financial economics , economics , metallurgy , catalysis
The title compound 1 reacts with trifluoroacetic anhydride to give the doubly trifluoracetylated derivative 2 and in addition the coumarin derivative 3 . In refluxing DMF, two moles of 1 react with loss of one molecule of ammonia to afford 4 , which undergoes subsequent N ‐acylation by β‐dicarbonyl compounds 9a‐f to yield N ‐acyl derivatives 10a‐f . With dimethyl malonate ( 9a ) besides compound 10a , the cycloacylated compound 11 was also obtained in good yield. Compound 11 is readily hydrolysed and decarboxylated with both acid and alkali to the previously described fused derivative 12 . The latter may be converted into the new thienopyrimidinone derivative by action of aqueous alkali.