Condensation reactions of 3-amino-4-imino-4H-thieno-[3,4-c][1]benzopyran

The title compound 1 reacts with trifluoroacetic anhydride to give the doubly trifluoracetylated derivative 2 and in addition the coumarin derivative 3. In refluxing DME two moles of 1 react with loss of one molecule of ammonia to afford 4, which undergoes subsequent N-acylation by beta-dicarbonyl c...

Full description

Saved in:
Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 33; no. 2; pp. 281 - 286
Main Authors NyiondiBonguen, E, Fondjo, ES, Fomum, ZT, Dopp, D
Format Journal Article
LanguageEnglish
Published TAMPA HETERO CORPORATION 01.03.1996
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet more information

Cover

More Information
Summary:The title compound 1 reacts with trifluoroacetic anhydride to give the doubly trifluoracetylated derivative 2 and in addition the coumarin derivative 3. In refluxing DME two moles of 1 react with loss of one molecule of ammonia to afford 4, which undergoes subsequent N-acylation by beta-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.
ISSN:0022-152X
DOI:10.1002/jhet.5570330212