Synthesis and Characterization of New 2-Thiophen 3'4-Dimethylbenzaldehyde As 3,4-Dihydropyrimidinone Derivatives

CENTRAL ASIAN JOURNAL OF MEDICAL AND NATURAL SCIENCES
Volume: 04 Issue: 05 | Sep-Oct 2023 ISSN: 2660-4159

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Synthesis and Characterization of New 2-Thiophen 3'4-

Dimethylbenzaldehyde as 3,4-Dihydropyrimidinone Derivatives
1. Lina Abdullah Naser Abstract:
Background: This study it has been successfully
synthesized and characterized in the form of [3,4-
Received 1st Jul 2023, dihydropyrimidin-2-(1H) ones] (1-3) a derivative. This
Accepted 15th Aug 2023,
Online 11th Sep 2023
compound were synthesized by reaction of 1,3-
cyclohexane dione in the presence of ethanol, urea, and
aromatic aldehyde(t-BuOK).It has been characterized
1
Southern Technical University, Nasiriyah spectroscopically (For example, 13C-NMR, 1H-NMR,
Technical Institute Nursing technology and FT-IR) For the purpose of showing the chemical
department, Iraq composition and the final result of the industrial
compound.
Methods: The design of this research was cross-
sectional. descriptive investigation,which included the
preparation of a group of polypyrimidine derivatives.
Results: In the current work, 1,3-cyclohexandione,
aromatic aldehydes, and urea are combined with ethanol
to create 3,4-Dihydropyrimidine. The chemical
composition of molecules was determined via spectral
analysis (1-2)a.
Conclusion: When t-BuOK was used as a catalyst in
this work to create three DHMP compounds, it produced
outstanding results with a high yield and a quicker
reaction time than the assistant factor.
Key words: Biginilli reaction with 3,4-
dihydropyrimidine-2-(1H)-ones.
Introduction
Several factors have led to the growing significance of Organic and pharmaceutical chemistry
multicomponent reactions (MCRs). Three or more compounds interacting simultaneously but
sequentially to create a new product known as an MCR condensation that retains all of the constituents
of all of its starting components.
New MCRs are being sought after and discovered, to name a few(2). Pietro Biginelli, an Italian
scientist, developed the Biginelli reaction in 1893. He discussed the reaction between an aldehyde and
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CAJMNS Volume: 04 Issue: 05 | Sep-Oct 2023
a -ketoester that is acid-catalyzed, and urea (or thiourea), and this process became known as the
Biginelli reaction (3).
More than a century ago, cleverly predicting the synthetic potential of multicomponent reactions,
Biginelli combined the reactants of two distinct processes that shared a component in a single flask(4).
A substituted 3,4-dihydropyrimidine-2(1H)-one (DHPM)(5), which was successfully recognized, was
the end product of the three-component reaction. In recent years, there has been a lot of focus on
improving the reaction catalyst (6).
Scheme(1) Biginelli reaction

Experimental
Iranian University of Isfahan 400 MHz BRUKER spectrophotometer used to record 1H-NMR
spectra.Using tetramethylsilane (TMS) as the internal standard and DMSO-d6 as the solvent, the
chemical shift values are presented in ppm. DMSO-d6 is used as the solvent and a BRUKER
spectrophotometer operating at 125 MHz is used to record 13C-NMR spectra. (ppm) units are used to
express the chemical shift values, and tetramethylsilane (TMS) is utilized as the internal standard. On
a Shimadzu IR Affinity-1, IR spectra were captured.
Polyhydropyrimidine(1-3)a synthesis: general process
Scheme2: General Synthesis of compounds (1-3)

4-(thiophen-2-yl)-4,6,7,8-tetrahydroquinazoline-2,5(1H,3H)-dione(2a):
The chemical was created through the reaction of urea, (0.9 g, 0.015 mol), and (0.875 ml, 0.01 mol) 2-
thiophene. (1.12gm, 0.01mole) of 1,3-cyclohexane dione , and (0.112 gm ,0.002 mole) of potassium
tet-Butoxide with (20ml)of ethanol as shown in scheme(2-6) .Milting point (194-196 ),yield
was(94.82). as shown scheme(4).
Scheme(3)
4-(furan-3-yl)-4,6,7,8-tetrahydroquinazoline-2,5(1H,3H)-dione(3a)
The reaction resulted in the compound's creation(0.86ml,0.01mole) of 3,4-dimethyl benzaldehyde, (0.9
gm,0.015mole ) of urea , (1.12gm, 0.002 mole) of 1,3-cyclohexane dione , and (0.112gm , 0.001 mole)
of potassium tet-Butoxide with (20ml)of ethanol as shown in scheme(2-8) .Milting point (201-208
),yield was(86.95). as shown scheme(5)
Scheme(5)
Figure(1): General structure of 3,4-dihydropyrimidine

RESULATS AND DISCUSION
The 3,4-Dihydropyrimidine derivatives' structural skeleton exhibits a wide range of biological
activities, making them useful as medicines (7), antibiotics (8) or herbicides (9), as well as as
antihypertensive (9) and antibacterial (10) agents. In the current study, 3,4-Dihydropyrimidine is
produced by reacting 1,3-cyclohexandione and aromatic aldehydes with urea in ethanol. Spectral
analysis was used to ascertain the chemical make-up of molecules (1-2)a, as depicted in Figure 2.
1a 2a 3a
Figure(2)
Five bands in the IR spectrum (KBr) of polyhydropyrimidine (1-3)a, including the carbonyl group
(C=O), the stretching vibration of aromatic and aliphatic C-H molecules and N-H amide, alkene
(2939-3109,2885-2870,1700-1720,3136-3294,1481-1466)(11)cm-1,respectively.
As indicated in table (1), a shared basic package represented by (NH)groups, (CH2)groups, and
(CH)groups was visible in the 1H-NMR spectra of the three compounds (1-3).In compound (1a) we
can notes multi signal δ (1.45,1,94,2.92) for C2,C1,C3 , a singlet signal for C4 showed δ(5.52), the
ring of phenyl it shown as (dd) signal at δ(7.29 and 7.34) ,amid groups was shown at δ(7.56 and 9.2).
compound (2a,3a) the substitution in the C4 is different as shown in table (1).The13C-NMR spectrum
of (1a) showed positive signal at Chemical δ(20.3,20,28,59) for (C1,C2,C3,C4),also signal at δ
(164,196) for carbonyl group in two cycle, The phenyl ring ultimately exhibits a positive signal at
chemical shift (126.1-141.4) as (dd).
The compound (2a,3a) have as same chemical shift with some differences as shown figure(2)
Tables 1-: 1H-NMR signals of polyhydropyrimidine derivatives
ppm chemical shift
Protons with an
Comp. Atomic Protons various protons
aroma
1a 1.67 (M,2H,CH2)C2 7.29(dd)N5 7.56(s,1H,NH)
1.94(t,2H,CH2)C1 7.36(dd)N6 7.34(s,1H,NH)
2.66(t,2H,CH2)C3
5.52(s,1H,CH)C4
2a 1.64(M,2H,CH2)C2 6.79 7.4(s,1H,NH)
1.96(t,2H,CH2)C1 7.3 9.56(s,1H,NH)
3,03(t,2H,CH2)C3 For thiophen ring
5.5(s,1H,CH)C4
3a 1.18(M,2H,CH2)C2 6.1 7.4(s,1H,NH)
1.98(t,2H,CH2)C1 7.4 10.4(s,1H,NH)
3.6(t,2H,CH2)C3 For 3-frural ring
5.3(s,1H,CH)C4
Acknowledgement: I easily express my heartfelt thanks to my children and friends for their continued
support and encouragement.
Conflict of interest
This study has no any reported conflict of interests for its results, population, or aims.
References
1. Domling,A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
2. Weber, L.; lllgen, K.; Almstetter, M. Synlett 1999, 3, 366.
3. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
4. Rovnyak,G.C.Kimball,S.D.Beyer B.Cucinotta,G.DiMarco, J. D.Gougoutas, J.
Z.Hedberg,A.Malley,M.F.McCarthy,J. P. Zhang, R.Moreland,S.J.Med. Chem. 1995, 38, 119 and
references therein.
5. D.S.Bose,M.Sudharshan,S.W. Chavhan.Organic Chemistry Division III, Fine Chemicals
Laboratory,Indian Institute of Chemical Technology, Hyderabad- 500 007, India ARKIVOC 2005
(iii) 228-236 .
6. M.M. Hosseini1.E.Kolvari1.N.Koukabi1.M.Ziyaei1.M.Zolfigol. 28 February 2016- Springer
Science+Business Media New York 2016
7. Cepanec, I. Litvić, M.Filipsn‐Litvić, M. Grüngold,I,2007,J. Tetrahedron,63, 11822.
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CENTRAL ASIAN JOURNAL OF MEDICAL AND NATURAL SCIENCES

Volume: 04 Issue: 05 | Sep-Oct 2023 ISSN: 2660-4159

Synthesis and Characterization of New 2-Thiophen 3'4-

33 Published by “ CENTRAL ASIAN STUDIES" http://www.centralasianstudies.org

Scheme(1) Biginelli reaction

Scheme2: General Synthesis of compounds (1-3)

34 Published by “ CENTRAL ASIAN STUDIES" http://www.centralasianstudies.org

Figure(1): General structure of 3,4-dihydropyrimidine

35 Published by “ CENTRAL ASIAN STUDIES" http://www.centralasianstudies.org

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37 Published by “ CENTRAL ASIAN STUDIES" http://www.centralasianstudies.org

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