Synthesis and characterization of novel pyrimidine derivatives of N-pentyl-2,7-diphenyl-3,8a-dihydroimidazo[1,2-a]pyrimidin-3-amine via 4-phenylpyrimidin-2-amine

• Authors: Kadachha Raju Ramade , Atul J. Rojivadiya , Yogesh T. Naliapara , Jayesh S. Babariya
• Languages of publication: EN

Abstracts

EN

The target compound N-pentyl-2,7-diphenyl-3,8a-dihydroimidazo[1,2-a]pyrimidin-3-amine have been synthesized by4-phenylpyrimidin-2-amine with Triflouro acetic acid and benzyldehyde. The obtained products were characterized by 1H NMR, Mass and IR Spectra. Purity of all the compounds has been checked on thin layer chromatographic plate and NMR analysis technique.

Keywords

EN

4-phenylpyrimidin-2-amine; N-pentyl-2.7-diphenyl-3.8a-dihydroimidazo[1.2-a]pyrimidin-3-amine; benzyldehyde; imidazole; pyrimidine; triflouro acetic acid

Discipline

• CHEMISTRY: CHEMISTRY

• Publisher: Scientific Publishing House „DARWIN”
• Journal: World News of Natural Sciences
• Year: 2021
• Volume: 37
• Pages: 92-101

Contributors

author

Kadachha Raju Ramade

• Department of Chemistry, Maharshi Dayanand Science College, Porbandar, Gujarat, India

author

Atul J. Rojivadiya

• Department of Chemistry, Maharshi Dayanand Science College, Porbandar, Gujarat, India

author

Yogesh T. Naliapara

• Department of Chemistry, Saurashtra University, Rajkot, Gujarat, India

author

Jayesh S. Babariya

• Department of Chemistry, Shree H.N. Shukla Group of Colleges, Rajkot, Gujarat, India

References

• [1] A. Aly (2006) Synthesis and Pharmacological Activity of Annelated Pyrimidine Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 181:6, 1285-1298, DOI: 10.1080/10426500500326792
• [2] Sobhi M. Gomha, Mohamed G. Badry, Mohamed M. Abdalla. (2016) Isoxazolopyrimidinethione and Isoxazolopyridopyrimidinethione Derivatives: Key Intermediates for Synthesis of Novel Fused Triazoles as Potent 5α-Reductase Inhibitors and Anti-Prostate Cancer. Journal of Heterocyclic Chemistry 53: 2, pages 558-565
• [3] Wafaa S. Hamama, Mohamed A. Ismail, Hanaa A. Al-Saman, Hanafi H. Zoorob. (2013) Facile construction of substituted pyrimido[4,5-d]pyrimidones by transformation of enaminouracil. Journal of Advanced Research 4: 2, pages 115-121
• [4] Xi-Cun Wang, Ying Wei, Yu-Xia Da, Zhang Zhang, Zheng-Jun Quan. (2011) One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide. Heterocycles 83: 12, pages 281
• [5] Esvet Akbas, Abdulkadir Levent, Selcuk Gumus, Mehmet Rauf Sumer, Inci Akyazi. (2010) Synthesis of Some Novel Pyrimidine Derivatives and Investigation of their Electrochemical Behavior. Bulletin of the Korean Chemical Society 31: 12, pages 3632-3638
• [6] Changsheng Yao, Song Lei, Cuihua Wang, Chenxia Yu, Shujiang Tu. (2008) Solvent-free synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5- a ]pyrimidine-6-carboxylic esters catalyzed by sulfamic acid. Journal of Heterocyclic Chemistry 45: 6, pages 1609-1613
• [7] Esvet Akbał, Furgan Aslanoǧlu, Ahmet Şener, Bariş Anil. (2008) A simple one-pot synthesis of 1,2,3,4-tetrahydro-2-thioxopyrimidine derivatives. Journal of Heterocyclic Chemistry 45: 5, pages 1457-1460
• [8] Esvet Akbaş, Furgan Aslanoğlu. (2007) Studies on Reactions of Pyrimidine Compounds. 21. Microwave-Assisted Synthesis of 1,2,3,4-Tetrahydro-2- Thioxopyrimidine Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 183:1, pages 82-89
• [9] Furgan Aslanoğlu, Esvet Akbaş, Mehmet Sönmez, Barış Anıl. (2007) Studies on Reactions of Pyrimidine Compounds: Synthesis and Reactions of 5-Benzoyl-4,6-Diphenyl-1,2,3,4-Tetrahydro-2-Thioxopyrimidine. Phosphorus, Sulfur, and Silicon and the Related Elements 182:7, pages 1589-1597
• [10] Shipra Baluja, Kajal Nandha, Paras Ramavat, Solubility of pyrimidine derivatives in different organic solvents at different temperatures. World Scientific News 44 (2016) 13-34
• [11] Hardik K. Senjani, H. D. Joshi, Synthesis and characterization of diversely substituted pyrimidine-3-carboxamide and their antimicrobial evaluation. World Scientific News 150 (2020) 39-77
• [12] Yogesh M. Ajudiya, Jayesh S. Babariya, J. J. Upadhyay, Synthesis and characterization of 2-(methylthio)-6-oxo-6H-chromeno[3,4-e]pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivatives. World Scientific News 123 (2019) 258-264
• [13] Gautamkumar Dhuda, Paresh Ladwa, Jayesh J. Modha, Gewald reaction for the synthesis of benzo[4,5]-thieno[2,3-d]pyrimidin-4(3H)-one derivatives and it’s antimicrobial study. World Scientific News 151 (2021) 110-122
• [14] Shantaram Gajanan Khanage, S. Appala Raju, Popat Baban Mohite, Ramdas Bhanudas Pandhare. Synthesis and Pharmacological Evaluation of Some New Pyrimidine Derivatives Containing 1,2,4-Triazole. Adv Pharm Bull. 2012 Dec; 2(2): 213–222. doi: 10.5681/apb.2012.033
• [15] Cieplik, J., Stolarczyk, M., Pluta, J., Gubrynowicz, O., Bryndal, I., Lis, T., & Mikulewicz, M. (2011). Synthesis and antibacterial properties of pyrimidine derivatives. Acta Poloniae Pharmaceutica, 68(1), 57–65
• [16] Kidwai, M.; Saxena, S.; Rastogi, S.; Venkataramanan, R. Pyrimidines as Anti-Infective Agents. Current Medicinal Chemistry - Anti-Infective Agents, Volume 2, Number 4, 2003, pp. 269-286. DOI: https://doi.org/10.2174/1568012033483015
• [17] Olga Bruno, Silvia Schenone, Angelo Ranise, Francesco Bondavalli, Elisabetta Barocelli, Vigilio Ballabeni, Milena Chiavarini, Simona Bertoni, Massimiliano Tognolini, Mariannina Impicciatore. New polycyclic pyrimidine derivatives with antiplatelet in vitro activity: synthesis and pharmacological screening. Bioorganic & Medicinal Chemistry, Volume 9, Issue 3, 2001, Pages 629-636, https://doi.org/10.1016/S0968-0896(00)00272-8
• [18] Burnstock, G. Purine and pyrimidine receptors. Cell. Mol. Life Sci. 64, 1471 (2007). https://doi.org/10.1007/s00018-007-6497-0
• [19] Zia Ul Haq Khan, Arif Ullah Khan, Pingyu Wan, Yongmei Chen, Dandan Kong, Shafiullah Khan & Kamran Tahir (2015) In vitro pharmacological screening of three newly synthesised pyrimidine derivatives. Natural Product Research, 29:10, 933-938, DOI: 10.1080/14786419.2014.964707
• [20] Zia Ul Haq Khan, Amjad Khan, Pingyu Wan, Arif Ullah Khan, Kamran Tahir, Nawshad Muhammad, Faheem Ullah Khan, Hidayat Ullah Shah, Zia Ullah Khan. (2018) New natural product -an efficient antimicrobial applications of new newly synthesized pyrimidine derivatives by the electrochemical oxidation of hydroxyl phenol in the presence of 2-mercapto-6-(trifluoromethyl) pyrimidine-4-ol as nucleophile. Natural Product Research 32: 10, pages 1161-1169
• [21] Nadieh Dorostkar-Ahmadi, Abolghasem Davoodnia, Niloofar Tavakoli-Hoseini, Hossein Behmadi, Mahboobeh Nakhaei-Moghaddam. (2019) Facile synthesis of new pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidin-5(1H)-ones via the tandem intramolecular Pinner–Dimroth rearrangement and their antibacterial evaluation. Zeitschrift für Naturforschung B 74: 2, pages 175-181
• [22] Nasrinsadat Hosseininasab, Abolghasem Davoodnia, Faramarz Rostami-Charati, Niloofar Tavakoli-Hoseini, Amir Khojastehnezhad. (2018) Synthesis of New Pyrimido[4′,5′:3,4]pyrazolo[1,2- b ]phthalazine-4,7,12-triones: Derivatives of a New Heterocyclic Ring System. Journal of Heterocyclic Chemistry 55: 1, pages 161-165
• [23] Salwa F. Mohamed, Alhusain A. Ibrahiem, Abd El-Galil E. Amr and Mohamed M. Abdalla, 2015. SARS-CoV 3C-Like Protease Inhibitors of some Newly Synthesized Substituted Pyrazoles and Substituted Pyrimidines Based on 1-(3-Aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one. International Journal of Pharmacology, 11: 749-756. DOI: 10.3923/ijp.2015.749.756
• [24] Abdel Mohsen HT, Ragab FAF, Ramla MM, El Diwani HI. 2010. Novel benzimidazole–pyrimidine conjugates as potent antitumor agents. Eur J Med Chem. 45(6): 2336–2344
• [25] Abu-Hashem AA, Youssef MM, Hussein HAR. 2011. Synthesis, antioxidant, antitumor activities of some new thi-azolopyrimidines, pyrrolothiazolo pyrimidines and tri azolopyrrolothiazolo pyrimidines derivatives. J Chin Chem Soc. 58: 41–48
• [26] Amin KM, Awadalla FM, Eissa AAM, Abou-Seri SM, Hassan GS. 2011. Design synthesis and vasorelaxant evaluation of novel coumarin–pyrimidine hybrids. Bioorg Med Chem. 19: 6087–6097
• [27] Chandrashekaran S, Nagarajan S. 2005. Microwave-assisted synthesis and anti-bacterial activity of some 2-amino-6-aryl-4-(2-thienyl) pyrimidines. IL Farmaco. 60: 2, 79–282
• [28] Falcao EPDaS, de Melo SJ, Srivastava RM, Catanho MT, Do Nascimento SC. 2006. Synthesis and anti-inflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines. Eur J Med Chem. 41: 276–282
• [29] Ingaral N, Saravanan G, Amutha P, Nagarajan S. 2007. Synthesis, in vitro antibacterial and antifungal evaluations of 2-amino-4-(1-naphthyl)-6-arylpyrimidines. Eur J Med Chem. 42: 517–520
• [30] Khan ZUH, Chen Y, Khan SU, Kong D, Liang MH, Wan P, Jin X. 2014. Electrochemical initiation of nucleophilic substitution of hydroquinone with 4,6-dimethylpyrimidine-2-thiol. Int J Electrochem Sci. 9: 4665–4674
• [31] Sirisoma N, Kasibthala S, Nguyen B, Pervin A, Wang Y, Claassen G, Tseng B, Drewe J, CaiSX. 2006. Discovery of substituted 4-anilino-2-(2-pyridyl) pyrimidine as a new series of apoptosis inducers using a cell- and caspase-based high throughput screening assay. Part 1: structure-activity relationships of the 4-aniline group. Bioorg Med Chem. 14: 7761–7773
• [32] Vega S, Alonso J, Diaz JA, Jonquiere F. 1990. Synthesis of 3-substituted-4-phenyl-2-thioxo-1,2,3,4,5,6,7,8-octahydrobenzo [4,5] thieno [2,3-d]pyrimidines. J Heterocycl Chem. 27:269–273
• [33] Shin Kamijo, Kaori Kamijo, and Toshihiro Murafuji. Synthesis of Alkylated Pyrimidines via Photoinduced Coupling Using Benzophenone as a Mediator. The Journal of Organic Chemistry 2017, 82 (5), 2664-2671. https://doi.org/10.1021/acs.joc.6b03058
• [34] Sumaiya Tabassum, K.R. Sunaja Devi, Santhosh Govindaraju. Nano ZnO@PEG catalyzed one-pot green synthesis of pyrano[2,3-d]pyrimidines in ethanol via one-pot multicomponent approach. Materials Today: Proceedings 2021, 45, 3716-3721. https://doi.org/10.1016/j.matpr.2020.12.677
• [35] Thuraka Sekhar, Pinnu Thriveni, Annavarapu Venkateswarlu, Thathapudi Daveedu, Kotha Peddanna, Sri Bhashyam Sainath, One-pot synthesis of thiazolo[3,2-a]pyrimidine derivatives, their cytotoxic evaluation and molecular docking studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 10.1016/j.saa.2020.118056, (118056), (2020)
• [36] Ajmal R. Bhat, Rajendra S. Dongre, Faisal A. Almalki, Malika Berredjem, Mohamed Aissaoui, Rachid Touzani, Taibi Ben Hadda, Mohammad S. Akhter, Synthesis, biological activity and POM/DFT/docking analyses of annulated pyrano[2,3-d]pyrimidine derivatives: Identification of antibacterial and antitumor pharmacophore sites. Bioorganic Chemistry, 10.1016/j.bioorg.2020.104480, (104480), (2020).
• [37] Alaa R. Sakr, Mohamed G. Assy, Youssra S. ELasaad, Design and chemical behavior of novel pyrimidine derivatives and their evaluation of cytotoxicity. Synthetic Communications, 10.1080/00397911.2020.1735444, (1-7), (2020).
• [38] S. Gajalakshmi, I. V. Asharani, D. Thirumalai, Synthesis and Antioxidant Activity of Functionalized Pyridinyl-Methylthiosemicarbazide Derivatives. Polycyclic Aromatic Compounds, 10.1080/10406638.2020.1866033, (1-10), (2020)
• [39] Kiran N. Patil, Rohan A. Mane, Sandip B. Jadhav, Mansing M Mane, Vasant B. Helavi, One pot multicomponent synthesis of highly functionalized tetrahydropyridine using copper (II) triflate as catalyst and their anti-inflammatory activity, Chemical Data Collections, 10.1016/j.cdc.2019.100233, (100233), (2019)
• [40] Meeta Sahu, Nadeem Siddiqui, Ramsha Iqbal, Vidushi Sharma, Sharad Wakode, Design, synthesis and evaluation of newer 5,6-dihydropyrimidine-2(1 H )-thiones as GABA-AT inhibitors for anticonvulsant potential, Bioorganic Chemistry, 10.1016/j.bioorg.2017.07.017, 74, (166-178), (2017)
• [41] Meeta Sahu, Nadeem Siddiqui, Mohd. Javed Naim, Ozair Alam, Mohammad Shahar Yar, Vidushi Sharma, Sharad Wakode, Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models, Archiv der Pharmazie, 10.1002/ardp.201700146, 350, 9, (2017)
• [42] Bagher Mohammadi, Microwave assisted one-pot pseudo four-component synthesis of 2,4,6-trisubstituted pyridines using γ-MnO2 nanoparticles. Monatshefte für Chemie - Chemical Monthly, 10.1007/s00706-016-1698-6, 147, 11, (1939-1943), (2016)

• Document Type: article