Abstract
2-acetyl-3-amino-4,6-dimethylthieno[2,3-b]pyridine 1 reacted with dimethoxy-tetrahydrofuran in acetic acid and ethyl cyanoacetate in the presence of ammonium acetate or with NaNO
2
in the presence of an AcOH/HCl mixture to produce 2-4. Compound 2 reacted with aromatic aldehydes, semicarbazide hydrochloride, thiosemicarbazide, and phenyl hydrazine or with hydrazine hydrate to give compounds 5a-c and 11a-d, respectively.
Chalcone 5 reacted with hydrazines, hydroxylamine hydrochloride, or thiourea to produce compounds 6-9. Thiosemicarbazone 11b reacted with α -haloester to produce the corresponding thiazolidinone derivatives 12a,
b
; also it reacted with ω -bromoacetophenone to give thiazoline derivatives 13a,
b
.