Synthesis of imidazo-1,4-oxazinone derivatives and investigation of reaction mechanism
Synthesis of imidazo-1,4-oxazinone derivatives and investigation of reaction mechanism
In this study, nine different C-2 aroyl imidazole derivatives were synthesized in a one pot reaction with two steps, and the reduction reactions of these derivatives with $NaBH_4$were carried out under mild conditions. Substitution reaction of obtained imidazo methanol derivatives with chloroacetylchloride reagent and ring reaction of substitution products were investigated. It was determined that 1,4-imidazoxazinone derivative was obtained as a result of the cyclization reaction. The intermediate products obtained during the cyclization reaction were isolated, and the path of the reaction under different conditions was discussed.
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- 1. Schröder K, Enthaler S, Bitterlich B, Schulz T, Spannenberg A et al. Design of and Mechanistic Studies on a Biomimetic Iron–Imidazole Catalyst System for Epoxidation of Olefins with Hydrogen Peroxide. Chemistry A European Journal 2009; 38 (15): 5471-5481. doi: 10.1002/chem.200802731
- 2. Jin Z. Muscarine, imidazole, oxazole, and thiazolealkaloids. The Royal Society of Chemistry 2011; 28 (6): 1143–1191. doi: 10.1039/ c0np00074d
- 3. Gao G, Xiao R, Yuan Y, Zhou C-He, You J et al. Efficient imidazolium catalysts for the benzoin Condensation. Journal of Chemical Research 2002; 2002 (6): 262–263. doi: 10.3184/030823402103172130
- 4. Farooq S, UlHaq I, Ullah N. Synthesis, characterization and biological evaluation of N-Mannich base derivatives of 2-phenyl-2-imidazoline as potential antioxidants, enzyme inhibitors, antimicrobials, cytotoxic and anti-inflammatory agents. Arabian Journal of Chemistry 2021; 14 (4): 103050. doi: 10.1016/j.arabjc.2021.103050
- 5. Mazik M, Hartmann A. Recognition properties of receptors consisting of imidazole and indole recognition units towards carbohydrates. Beilstein Journal of Organic Chemistry 2010; 6 (9): 1-10. doi: 10.3762/bjoc.6.9
- 6. Choi J-H, Abe N, Tanaka H, Fushimi K, Nishina Y et al. Plant-Growth Regulator, Imidazole-4-Carboxamide, Produced by the Fairy Ring Forming Fungus Lepista sordida. Journal of Agricultural and Food Chemistry 2010; 58 (18): 9956-9959. doi: 10.1021/jf101619a
- 7. Emandia G, Flanagana KJ, Sengea MO. Fluorescent imidazole-based chemosensors for the reversible detection of cyanide and mercury ions. Photochemical & Photobiological Sciences 2018; 17: 1450-1461. doi:10.1039/C8PP00226F
- 8. ChengHe Z, LinLing G, YiYi1 Z, FeiFei Z, GuangZhou1 W et al. Review on supermolecules as chemical drugs. Science in China Series B: Chemistry 2009; 52 (4): 415-458. doi: 10.1007/s11426-009-0103-2
- 9. Niedzicki L, Zukowska G.Z, Bukowskaa M, Szczecinski P, Grugeonb S et al. New type of imidazole based salts designed specifically for lithium ion batteries. Electrochimica Acta 2010; (55): 1450-1454. doi: 10.1016/j.electacta.2009.05.008
- 10. Jacques P, Graff B, Diemer V, Ay E, Chaumeil H et al. Negative solvatochromism of a series of pyridinium phenolate betaine dyes with increasing steric hindrance. Chemical Physics Letters 2012; 531: 242–246. doi: 10.1016/j.cplett.2012.02.018
- 11. Fu N, Zhang L, Luo S, Chenga J-P. Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones. Organic Chemistry Fronttiers 2014; 1: 68-72. doi: 10.1039/C3QO00027C]
- 12. Taşdemir V, Kuzu B, Tan M, Genç H, Menges N. Copper-Catalyzed Synthesis of Fused Imidazopyrazine N-Oxide Skeletons. Synlett 2019; 30 : 307-311. doi:10.1055/s-0037-1610859
- 13. Calvino-Casilda V, Banares MA. In situ Raman monitoring of Michael addition for the synthesis of 1-substituted imidazoles intermediates with antiviral properties. Catalysis Today 2012; 187: 191-194. doi: 10.1016/j.cattod.2011.09.006
- 14. Mombelli PL, Chapelain C, Munzinger N, Joliat E, İllarionov B et al. Imidazole-and Benzimidazole-Based Inhibitors of the IspE: Targeting the Substrate-Binding Site and the Triphoshate-Binding Loop of the ATP Site. European Journal of Organic Chemistry 2013; 1068-1079. doi: 10.1002/ejoc.201201467
- 15. Kuzu B, Tan M, Ekmekci Z, Menges N. A novel structure for ESIPT emission: Experimental and theoretical İnvestigations. Journal of Photochemistry & Photobiology A: Chemistry 2019; 381: 11874. doi: 10.1016/j.jphotochem.2019.111874
- 16. Zhang L, Peng X-Mei, Damu GLV, Geng R-Xia, Zhou C-He. Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry. Medicinal Research Reviews 2014; 34 (2): 340–437. doi: 10.1002/med.21290
- 17. Tippannanavar, M, Verma, A, Kumar R, Gogoi R, Kundu A et al. Preparation of nanofungicides based on imidazole drugs and their antifungal evaluation. Journal of Agricultural and Food Chemistry 2020; 68 (16): 4566−4578. doi: 10.1021/acs.jafc.9b06387
- 18. Nagaraj M, Muthusubramanian S, Transition metal-free, base-promoted hydroalkoxylation: Synthesis of Substituted imidazo[2,1-c][1,4] oxazines. Jouranal of Chemistry Scientific. 2016; 128 (3): 451-458. doi: 10.1007/s12039-016-1045-9
- 19. Kuzu B, Genc H, Taspinar M, Tan M, Menges N. An easy synthetic protocol for imidazo-1,4-oxazines and evaluation of their toxicities. Heteroatom Chemistry 2018; 29: 1-12. doi: 10.1002/hc.21412
- 20. Ashtekar DR, C-Perira R, Nagrajan K, Vishvanathan N, Bhatt AD et al. In vitro and in vivo activities of the nitroimidazole cgi 17341 against mycobacterium tuberculosis. Antimicrobial Agents and Chemotherapy 1993; 37 (2): 183-186. doi: 10.1128/aac.37.2.183
- 21. Eftekhari-Sis B, Zirak M, Akbari A. Arylglyoxals in Synthesis of Heterocyclic Compounds. Chemical Reviews 2013; 113 (5): 2958-3043. doi: 10.1021/cr300176g
- 22. Khalili B, Jajarmi P, Eftekhari-Sis B, Hashemi MM. Novel one-pot, three-component synthesis of new 2-Alkyl-5-aryl-(1H)-pyrrole-4-ol in water. The Journal of Organic Chemistry 2008; 73 (6): 2090-2095. doi: 10.1021/jo702385n
- 23. Eftekhari-Sis B, Akbari1 A, Amirabedi M. Synthesis of new N-Alkyl(Aryl)-2,4-Diaryl-1H-Pyrrol-3-ols via aldol paal-knorr reactions. Chemistry of Heterocyclic Compounds 2010; 46 (11): 1330-1334. doi: 10.1007/s10593-011-0669-4
- 24. Mirko R, Manoj K. P, Alberto R, Valentina Z. sodium channel blocking activity and in-vivo testing of new phenylimidazole derivatives. Letters in Drug Design and Discovery 2016; 13 (9): 962-967. doi: 10.2174/1570180813666160714125755
- 25. Kuzu B, Tan M, Taslimi P, Gülçin İ, Taşpınar M et al. Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases. Bioorganic Chemistry 2019; 86 :187-196. doi: 10.1016/j.bioorg.2019.01.044
- 26. Martinez R, Pastor M.I, Yus M. 1,2-Functionalized imidazoles as palladium ligands: an efficient and robust catalytic system for the fluorine-free hiyama reaction. European Journal of Organic Chemistry 2014; 2014 (4): 872-877. doi: 10.1002/ejoc.201301439
- 27. Kuzu B, Taşdemir V, Menges N. Alkene or Alkyne-linked Imidazole Derivatives and Investigation of Their Applications. İn: 7th Drug Chemistry Conference: Design, Synthesis, Production and Standardization of Drug Active Substances, Antalya, Turkey, 2019.
- 28. Mishra D, Singh R, Rout C. A facile amidation of chloroacetyl chloride using DBU. International Journal of ChemTech Research 2017; 10 (3): 365-372.
- 29. Choi J, Lee J-O, Kim M-S, Nam SJEN, Chun K-H. Preparation of Morpholine-2-one and 1,4-Oxazepan-2-one Derivatives by Cyclization Reaction between N-Bts Amino Alcohol and Chloroacetyl Chloride. Bulletin Korean Chemical Society 2008; 29 (8): 1443-1444. doi: 10.5012/bkcs.2008.29.8.1443
- 30. Gao B, Wang L, Du R. Studies on Chloroacylation Reaction Process of Crosslinked Polystyrene Microspheres with ω- Chloroacyl Chloride as Reagent. Journal of Macromolecular Science Part A: Pure and Applied Chemistry 2010; 47 (9): 927-934. doi: 10.1080/10601325.2010.501677
- 31. Kiamehr M, Moghaddam FM, Erami MS. A convenient synthesis of 3-formyl-2-thioacetamide-indole derivatives via the one-pot reaction of indolin-2-thiones, isocyanides and chloroacetylchloride. Tetrahedron Letters 2015; 56 (52): 7190-7192. doi: 10.1016/j.tetlet.
- 32. Sing K.S, Manne N, Pal M. Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2- carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors. Beilstein Journal of Organic Chemistry 2008; 4 (20): 1-5. doi: 10.3762/bjoc.4.20
- 33. Viktor V. Efimov V.V, Krasnov P.O, Lyubyashkin A.V, Suboch G.A et al. Experimental and theoretical study of the acylation reaction of aminopyrazoles with aryl and methoxymethyl substituents. Journal of Molecular Structure 2018; 1165: 370-375. doi: 10.1016/j. molstruc.2018.04.018
- 34. Fikry R, Ismail N, Raslan S, El-Tahawe H. Synthesıs and Reactions of New Pyrazole Derivatives. European Chemical Bulletin 2016; 5 (5): 157-162. doi: 10.17628/ECB.2016.5.157
- 35. Toma T, Shimokawa J, Fukuyama T. N,N-Ditosylhydrazine: A Convenient Reagent for Facile Synthesis of Diazoacetates. Organic Letters 2007; 9 (16): 3195-3197. doi: 10.1021/ol701432k
- 36. Balcı M. Nükleer Manyetik Rezonans Spektroskopisi. Ankara, Türkiye: ODTÜ Yayıncılık, 2004.