Open Access Open Access  Restricted Access Subscription Access


М. Н. Курмач, А. Б. Рябицкий, В. Н. Брицун
Cover Image


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


2-acylthioamides, aromatic aldehydes, ureas, thioureas, three-component heterocyclization

Full Text: PDF (Russian) Supplementary File(s): None



Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia -