Microwave-Assisted Synthesis of New Dihydropyrimidine Derivatives and Mechanism of the Reactions

Akbaş E., ŞAHİN E., YILDIZ E., ANIL B., AKYAZI I.

LETTERS IN ORGANIC CHEMISTRY, cilt.10, sa.9, ss.651-656, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 10 Sayı: 9
  • Basım Tarihi: 2013
  • Doi Numarası: 10.2174/15701786113109990038
  • Dergi Adı: LETTERS IN ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.651-656
  • Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

5-benzoyl-4-aryl-6-phenyl-1,2,3,4-tetrahydro-2-thioxopyrimidines were synthesized via Biginelli cyclocondensation reaction. The diethyl 2-(4-aryl-5-benzoyl-6-phenyl-3,4-dihydropyrimidin-2(1H)-ylidene) malonates were prepared by the reaction of thioxopyrimidines with diethyl 2-bromomalonate in dioxane/pyridine (10/1 v:v) under microwave irradiation and conventional conditions. The reaction of diethyl 2-(5-benzoyl-4,6-phenyl-3,4-dihydropyrimidin-2(1H)ylidene) malonate with hydrazine hydrate and urea yielded the compounds of (E)-ethyl 2-(5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-ylidene)-3-hydrazinyl-3-oxopropanoate and (E)-ethyl 2-(5-benzoyl-4,6-diphenyl-3,4dihydropyrimidin-2(1H)-ylidene)-3-oxo-3-ureidopropanoate, respectively. All of these new derivatives were characterized by analytical and spectroscopic studies. The structure of the diethyl 2-(5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-lidene) malonate was identified by a single crystal X-ray diffraction analysis, and the reaction mechanism was also discussed.