H. Maruoka et al., STUDIES ON HETEROCYCLIC ENAMINONITRILES .15. A CONVENIENT ONE-POT SYNTHESIS OF ETHYL O-2,3-DIHYDROTHIENO-[2,3-B]PYRIDINE-5-CARBOXYLATES, Liebigs Annalen der Chemie, (12), 1993, pp. 1269-1271
The reaction of 2-amino-4,5-dihydro-3-thiophenecarbonitriles 1a-c with
ethyl acetoacetate in the presence of titanium(IV) chloride gave the
corresponding ethyl hydro-6-methylthieno[2,3-b]pyridine-5-carboxylates
3a-c. Similarly, compounds 1a-c reacted with diethyl malonate or ethy
l cyanoacetate to give the corresponding ethyl trahydro-6-oxothieno[2,
3-b]pyridine-5-carboxylates 4a-c or ethyl no-2,3-dihydrothieno[2,3-b]p
yridine-5-carboxylates 5a-c.