Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives

BAYRAMOĞLU D., KURTAY G., GÜLLÜ M.

SYNTHETIC COMMUNICATIONS, cilt.50, sa.5, ss.649-658, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 50 Sayı: 5
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1080/00397911.2019.1705349
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, EMBASE
  • Sayfa Sayıları: ss.649-658
  • Anahtar Kelimeler: 2-Aminopyrimidine, barbituric acid, cyclization reaction, sonochemistry, EFFICIENT SYNTHESIS
  • Ankara Üniversitesi Adresli: Evet

Özet

Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (similar to 30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, H-1-NMR techniques, and the obtained data were also checked from the previously published studies.