An efficient one-pot, three-component synthesis of 6-cyano-hexahydro-4$H$-thieno[3',2':5,6]pyrimido[1,2-$a$]quinoline-2-carboxylates and their spiro derivatives from $\beta $-enaminones

Authors

SAID AHMED SOLIMAN GHOZLAN
DOAA MOHMED ABDELMONIEM
AMR MOHMED ABDELMONIEM
ISMAIL ABDELSHAFY ABDELHAMID

Abstract

A simple and efficient one-pot synthesis of novel thieno[3',2':5,6]pyrimido[1,2-a]quinoline-2-carboxylates (5a-d) and their spirooxindole derivatives (12a-d) was accomplished. Thus, the Michael addition reaction of the cyclic $\beta $-enaminone 3 with the corresponding $\alpha ,\beta $-unsaturated nitrile derivatives 4a-d in refluxing EtOH in the presence of piperidine afforded 5a-d in good yields. On the other hand, spirooxindole derivatives 12a-d were synthesized by the reaction of cyclic $\beta $-enaminone 3 with the corresponding 3-cyanomethylidene-2-oxoindoles 11a-d in refluxing EtOH.

DOI

10.3906/kim-1507-31

Keywords

Cyclic enaminones, $\alpha$, $\beta$-unsaturated nitriles, hexahydroquinolines, multicomponent reaction, spirooxindoles

First Page

434

Last Page

440

Recommended Citation

GHOZLAN, SAID AHMED SOLIMAN; ABDELMONIEM, DOAA MOHMED; ABDELMONIEM, AMR MOHMED; and ABDELHAMID, ISMAIL ABDELSHAFY (2016) "An efficient one-pot, three-component synthesis of 6-cyano-hexahydro-4$H$-thieno[3',2':5,6]pyrimido[1,2-$a$]quinoline-2-carboxylates and their spiro derivatives from $\beta $-enaminones," Turkish Journal of Chemistry: Vol. 40: No. 3, Article 7. https://doi.org/10.3906/kim-1507-31
Available at: https://journals.tubitak.gov.tr/chem/vol40/iss3/7