2-ACYLTHIOAMIDES IN THE BIGINELLI REACTION

Abstract

It was shown for the first time that 2-acylthioamides enter the Biginelli reaction with aromatic aldehydes and ureas/thioureas producing N‑Ar¹‑4-Ar²-6-R¹-1-R²-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5‑carbothioamides. The regioselectivity of the process is in agreement with the hard and soft Lewis acid and base theory. It was established that under action of nitrous acid or other oxidants on the obtained products N‑Ar¹-4‑Ar²-6‑R¹-1-R²-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5‑carboxamides are formed, but not the expected 4‑Ar²-6-R¹-1-R²-5‑(1,3‑benzothiazol-2-yl)-1,2,3,4‑tetrahydropyrimidin-2-оnes(thiones).

How to Cite
Kurmach, M. N.; Ryabitskiy, A. B.; Britsun, V. N. Chem. Heterocycl. Compd. 2014, 49, 1770. [Khim. Geterotsikl. Soedin. 2013, 1910.]

For this article in the English edition see DOI 10.1007/s10593-014-1429-z