Citation: Mohamed S.A. El-Gaby, Jehan A. Micky, Nadia M. Saleh, Yousry A. Ammar, Heba S.A. Mohamed. Synthesis and spectroscopic characterization of novel 2-amino-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidine and pyrimido[1,2-a]pyrimidine derivatives[J]. Chinese Chemical Letters, ;2015, 26(6): 690-694. doi: 10.1016/j.cclet.2015.04.003 shu

Synthesis and spectroscopic characterization of novel 2-amino-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidine and pyrimido[1,2-a]pyrimidine derivatives

1.
a Chemistry Department, Faculty of Science, Al-Azhar University at Assiut, 71524 Assiut, Egypt;
2.
b Chemistry Department, Faculty of Science (Girl's), Al-Azhar University, Nasr City, Cairo, Egypt;
3.
c Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt;
4.
d Photochemistry Department, National Research Center, El-Dokki, Giza, Egypt

Corresponding author: Mohamed S.A. El-Gaby,
Received Date: 1 December 2014
Available Online: 17 March 2015

2-Aminocyclopenta[d]pyrimidines 3a-c were achieved via a one-pot, three-component reactions of cyclopentanone 1, aromatic aldehyde and guanidine hydrochloride (1:2:1 molar ratio). Also, cyclization of 2,5-bis-(arylmethylidene)cyclopentanones 2 with guanidine hydrochloride (1:1 molar ratio) in methanol in the presence of sodiummethoxide afforded cyclopenta-[d]pyrimidines 3. Compound 3a has been shown to be a useful building block for the synthesis of some novel pyrimido[1,2-a]pyrimidines 5, 7 and 12. The structures of the newly synthesized compounds were confirmed on the basis of analytical and spectral data.
- Multicomponent reaction,
- Cyclopenta[d]pyrimidine,
- Pyrimido[1,2-a]pyrimidine,
- Cyclopentanone
1. [1]
  [1] A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II, Pergamon Press, Oxford, 1996.
2. [2]
  [2] I.M. Lagoja, Pyrimidines as constituent of natural biologically active compounds, Chem. Biodivers. 2 (2005) 1-50.
3. [3]
  [3] (a) H. Kakiya, K. Yagi, H. Shinokubo, et al., Reaction of a, a-dibromo oxime ethers with Grignard reagents: alkylative annulation providing a pyrimidine core, J. Am. Chem. Soc. 124 (2002) 9032-9033; (b) M. Movassaghi, M.D. Hill, Single-step synthesis of pyrimidine derivatives, J. Am. Chem. Soc. 128 (2006) 14254-14255.
4. [4]
  [4] G.L. Luo, L. Chen, G.S. Poindexter, Microwave-assisted synthesis of aminopyrimidines, Tetrah. Lett. 43 (2002) 5739-5742.
5. [5]
  [5] A.R. Katritzky, B.V. Rogovoys, Recent developments in guanylating agents, Chem. Inform. 36 (2005) 49-87.
6. [6]
  [6] W.X. Zhang, Z.M. Hou, Catalytic addition of alkyne C-H, amine N-H, and phosphine P-H bonds to carbodiimides: an efficient route to propiolamidines, guanidines, and phosphaguanidines, Org. Biomol. Chem. 6 (2008) 1720-1730.
7. [7]
  [7] C. Alonso-Moreno, A. Antinolo, F. Carrillo-Hermosilla, A. Otero, Guanidines: from classical approaches to efficient catalytic syntheses, Chem. Soc. Rev. 43 (2014) 3406-3425.
8. [8]
  [8] W.X. Zhang, L. Xu, Z.F. Xi, Recent development of synthetic preparation methods for guanidines via transition metal catalysis, Chem. Commun. 51 (2015) 254-265.
9. [9]
  [9] S. Pirc, D. Bevk, A. Golobič, B. Stanovnik, J. Svete, Transformation of amino acids into nonracemic 1-(heteroaryl)ethanamines by the ignominiousketone methodology, Helv. Chim. Acta 89 (2006) 30-44.
10. [10]
  [10] E. Bellur, P. Langer, Synthesis of 4-(3-hydroxyalkyl)pyrimidines by ring transformation reactions of 2-alkylidenetetrahydrofurans with amidines, Tetrahedron 62 (2006) 5426-5434.
11. [11]
  [11] D. Hawksley, D.A. Griffin, F.J. Leeper, Synthesis of 3-deazathiamine, J. Chem. Soc. Perkin. Trans. I 1 (2001) 144-148.
12. [12]
  [12] N. Singh, S.K. Pandey, N. Anand, et al., Synthesis, molecular modeling and bioevaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents, Bioorg. Medic. Chem. Lett. 21 (2011) 4404-4408.
13. [13]
  [13] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiely-VCH, Weinheim, Germany, 2005.
14. [14]
  [14] C. Simon, T. Constantieux, J. Rodriguez, Utilisation of 1, 3-dicarbonyl derivatives in multicomponent reactions, Eur. J. Org. Chem. 2004 (2004) 4957-4980.
15. [15]
  [15] N. Isambert, M.S. Duque, J.C. Plaquevent, et al., Multicomponent reactions and ionic liquids: a perfect synergy for eco-compatible heterocyclic synthesis, Chem. Soc. Rev. 40 (2011) 1347-1357.
16. [16]
  [16] B.B. Touré, D.G. Hall, Natural product synthesis using multicomponent reaction strategies, Chem. Rev. 109 (2009) 4439-4486.
17. [17]
  [17] M.S.A. El-Gaby, G.A.M. El-Hag Ali, A.A. El-Maghraby, M.T.A. El-Rahman, M.H.M. Helal, Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4, 4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones, Eur. J. Med. Chem. 44 (2009) 4148-4152.
18. [18]
  [18] M.S.A. El-Gaby, Z.H. Ismail, S.M. Abdel-Gawad, H.M. Aly, M.M. Ghorab, Synthesis of thiazolidinone and thiophene derivatives for evaluation as anticancer, Phosph., Sulf. Silic. Rel. Elem. 184 (2009) 2645-2654.
19. [19]
  [19] M.S.A. El-Gaby, S.I. Mohamed, H.A. Eyada, et al., New approach for the synthesis of pyrano[2, 3-d]thiazoles, J. Mater. Sci. Eng. A1 (2011) 705-710.
20. [20]
  [20] M.S. Abaee, M.M. Mojtahedi, S. Forghani, et al., A green, inexpensive and efficient organocatalyzed procedure for aqueous aldol condensations, J. Braz. Chem. Soc. 20 (2009) 1895-1900.
21. [21]
  [21] M.S.A. El-Gaby, A.M. Hussein, A.A. El-Adasy, et al., Synthesis and biological evaluation of novel substituted furan, pyrimidine and pyrimido[1,2-a]pyrimidine derivatives having diphenyl sulfide moiety, Int. J. Pharm. Sci. 4 (2014) 780-786.
1. [1]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
2. [2]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
3. [3]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
4. [4]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
5. [5]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
6. [6]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
7. [7]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
8. [8]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
9. [9]
  Yu-Yao Li , Xiao-Hui Li , Zhi-Xuan An , Yang Chu , Xiu-Li Wang . Room-temperature olefin epoxidation reaction by two 2D cobalt metal-organic complexes under O₂ atmosphere: Coordination and structural regulation. Chinese Chemical Letters, 2025, 36(4): 109716-. doi: 10.1016/j.cclet.2024.109716
10. [10]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
11. [11]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
12. [12]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
13. [13]
  Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
14. [14]
  Huan Hu , Ying Zhang , Shi-Shuang Huang , Zhi-Gang Li , Yungui Liu , Rui Feng , Wei Li . Temperature- and pressure-responsive photoluminescence in a 1D hybrid lead halide. Chinese Journal of Structural Chemistry, 2024, 43(10): 100395-100395. doi: 10.1016/j.cjsc.2024.100395
15. [15]
  Hongren RONG , Gexiang GAO , Zhiwei LIU , Ke ZHOU , Lixin SU , Hao HUANG , Wenlong LIU , Qi LIU . High-performance supercapacitor based on 1D cobalt-based coordination polymer. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1183-1195. doi: 10.11862/CJIC.20250034
16. [16]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
17. [17]
  Xudong Zhao , Yuxuan Wang , Xinxin Gao , Xinli Gao , Meihua Wang , Hongliang Huang , Baosheng Liu . Anchoring thiol-rich traps in 1D channel wall of metal-organic framework for efficient removal of mercury ions. Chinese Chemical Letters, 2025, 36(2): 109901-. doi: 10.1016/j.cclet.2024.109901
18. [18]
  Gen Zhang , Ying Gu , Lin Li , Fuli Ma , Dan Yue , Xiaoguang Zhou , Chungui Tian . Anion-modulated HER and OER activity of 1D Co-Mo based interstitial compound heterojunctions for the effective overall water splitting. Chinese Chemical Letters, 2025, 36(7): 110110-. doi: 10.1016/j.cclet.2024.110110
19. [19]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
20. [20]
  Yu-Chen Fang , Jia-He Chen , Mi-Zhuan Li , Hui-Min Li , Mei Bai , Yong-Zheng Chen , Zi-Wei Gao , Wen-Yong Han . Forging of silaoxycarbocyclics by interrupted Catellani reaction. Chinese Chemical Letters, 2025, 36(7): 110474-. doi: 10.1016/j.cclet.2024.110474

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(835)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142