The use of anilinodihydrofurans in the synthesis of novel heterocyclic compounds

M. Hammouda, Z. M. Abou Zeid, H. A. Etman, M. A. Metwally
2011 Chemistry of Heterocyclic Compounds  
Alkyl 4-oxo-2-phenylamino-4,5-dihydrofuran-3-carboxylates were used for the preparation of alkyl 5-amino-7-aryl-2-{[aryl( hydroxy) methyl]( phenyl) amino}-4,6dicyano-1-benzofuran-3-carboxylates, 4-oxo-2-phenylamino-N-(p-tolyl)-4,5dihydrofuran-3-carboxamide, and ethyl 4-chloro-5-formyl-2-(phenylamino)furan-3carboxylate. The latter was used for the synthesis of ethyl 4-chloro-5-(hydrazinylidenemethyl)-2-(phenylamino)furan-3-carboxylate and diethyl 5,5'- Abstract
more » ... amide (1) was utilized for the synthesis of several new arylazocarbazole derivatives (2a-e). Compound (1) reacted with phenyl isothiocyanate to yield the corresponding non-isolable intermediate (3) , which gave, upon treatment with dilute hydrochloric acid, thiocarbamoyl derivative (4). Compound (3) reacted with chloroacetone, chloroacetic acid, chloroacetyl chloride, ethyl bromoacetate, and phenacyl bromide to afford thiazolone derivatives (6), (8), and (10), respectively. Compound (1) was heated in the presence of pyridine and/or hydrazine hydrate and/or isatine to give the corresponding tetrahydrocarbazole derivatives (13), (14) , and (18), respectively.
doi:10.1007/s10593-011-0714-3 fatcat:t3u65moisvgbjd6agrci5t7irm