Sains Malaysiana 53(4)(2024): 839-850

http://doi.org/10.17576/jsm-2024-5304-09

 

Synthesis and Characterization of Hexahydropyrimidines and Their New Derivatives

(Sintesis dan Pencirian Heksahidropirimidina serta Terbitan Baharunya)

 

SHUKKUR A. HAMED1, ATHRAA THAKER1, BILAL MAJID RUDAINI2, HASANAIN SALAH NAEEM3, MUNTAZ ABU BAKAR4 & SITI AISHAH HASBULLAH4,*

 

1Department of Chemistry, College of Education for Pure Science, University of Anbar, Al-Anbar, Iraq

2Department of Pharmacy, Al-Maarif University College, Al Anbar,31001, Iraq

3Faculty of Pharmacy, University of Al Muthanna, Samawah 66001, Iraq

4Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Selangor 43600, Malaysia

 

Received: 8 September 2023/Accepted: 29 February 2024

 

Abstract

Three new hexahydropyrimidine derivatives 1a – 1c were successfully synthesized using the Mannich-type reaction. Furthermore, the synthesis of three amino bases 2a2c was achieved through the reduction reaction of pyrimidine compounds using hydrazine, followed by the substitution reaction of nitro groups at diverse positions. Subsequently, one of the synthesized amino base derivatives 2c underwent conversion into seven Schiff bases 3a 3g via a condensation reaction involving the aforementioned amino base derivative and a selection of benzaldehyde derivatives. Four amide compounds 4a – 4d have been synthesized by a reaction of the secondary amine group in the pyrimidine ring with benzoyl chloride. The products were subjected to comprehensive characterization employing rigorous analytical techniques, including FT-), 1H-NMR (Proton Nuclear Magnetic Resonance Spectroscopy), and LC-MS (Liquid Chromatography–Mass Spectrometry). Additionally, the Molecular Electrostatic Potential (MEP) study was carried out to further investigate the properties of the synthesized compounds. The yields of the three methods used to synthesise new hexahydropyrimidine derivatives varied depending on the specific substituents added to the aromatic ring.

 

Keywords: Hexahydropyrimidine; Mannich-type reaction; Molecular Electrostatic Potential; Schiff-Bases

 

Abstrak

Sebanyak tiga terbitan heksahidropirimidin 1a1c telah berjaya disintesis menggunakan tindak balas jenis-Mannich. Selain itu, sintesis tiga bes amino 2a2c telah berjaya dijalankan melalui tindak balas penurunan sebatian pirimidina menggunakan sebatian hidrazina, diikuti oleh tindak balas penukargantian oleh kumpulan nitro pada posisi berlawanan. Sebatian 2c telah ditukarkan kepada tujuh bes Shiff 3a3g melalui tindak balas kondensasi melibatkan terbitan bes amino dan terbitan benzaldehid terpilih. Empat sebatian amida 4a4d telah disintesis melalui tindak balas kumpulan amina sekunder pada gelang pirimidina dengan benzoil klorida. Hasil kemudian dicirikan secara komprehensif melibatkan kepelbagaian teknik termasuk FT-IR (Spektroskopi Inframerah Fourier Transform), 1H-NMR (1H-Spektroskopi Nuklear Magnetik Resonan) dan LC-MS (Cecair Kromatografi–Spektrometri Jisim). Tambahan pula, kajian Potensi Elektrostatik Molekular (MEP) telah dijalankan untuk mengkaji dengan lebih mendalam ciri sebatian yang disintesis. Hasil yang diperoleh daripada tiga kaedah berbeza daripada sintesis sebatian baharu terbitan heksahidropirimidina menunjukkan variasi bergantung kepada penukarganti pada gelang aromatik.

 

Kata kunci: Bes-Schiff; heksahidropirimidina; Potensi Elektrostatik Molekul; tindak balas jenis Mannich

 

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*Corresponding author; email: aishah80@ukm.edu.my

 

 

 

 

 

 

 

 

 

 

 

 

 

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