Synlett, Inhaltsverzeichnis Synlett 2018; 29(12): 1627-1633DOI: 10.1055/s-0037-1609967 letter © Georg Thieme Verlag Stuttgart · New YorkZnO-Nanoparticles-Catalyzed Synthesis of Poly(tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-ones) as Novel Multi-armed Molecules Authors Institutsangaben Hadeer M. Diab Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt eMail: ismail_shafy@yahoo.com eMail: aelwahy@hotmail.com Ismail A. Abdelhamid* Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt eMail: ismail_shafy@yahoo.com eMail: aelwahy@hotmail.com Ahmed H. M. Elwahy* Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt eMail: ismail_shafy@yahoo.com eMail: aelwahy@hotmail.com Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Dedicated to Professor Klaus Hafner on the occasion of his 90th birthday Abstract A new series of poly(tetrahydrobenzimidazo[2,1-b]-quinazolin-1(2H)-ones) was synthesized in good yields using a multicomponent reaction of poly(aldehydes), dimedone, and 2-aminobenzimidazole in DMF under conventional heating as well as under microwave irradiation. Key words Key wordspoly(aldehydes) - 2-aminobenzimidazole - cyclocondensation - Michael addition - poly(alkylation) - poly(tetrahydrobenzimidazoquinazolinone) Volltext Referenzen References and Notes 1 Sinkkonen J. Ovcharenko V. Zelenin KN. Bezhan IP. Chakchir BA. Al-assar F. Pihlaja K. Eur. J. Org. Chem. 2002; 2046 2 Alagarsamy V. Pathak US. Bioorg. Med. Chem. 2007; 15: 3457 3 Alagarsamy V. 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RSC Adv. 2016; 6: 50431 79 Compound 7 was obtained by heating a mixture of 4-formylbenzoic acid (11, 1 mmol), dimedone (2, 1 mmol), and aminobenzimidazole (3, 1 mmol) in DMF (10 mL) at reflux for 1 h. The crude solid was isolated and recrystallized from DMF as colorless crystals (82%); mp > 300 °C. 1H NMR (300 MHz, DMSO-d6 ): δ = 0.91 (s, 3 H, CH3), 1.06 (s, 3 H, CH3), 2.02–2.23 (m, 2 H, CH2), 2.61–2.67 (m, 2 H, CH2), 6.49 (s, 1 H, H12), 6.95–7.95 (m, 8 H, Ar-H), 11.60–12-81 (br, 2 H, NH, COOH). MS (EI): m/z = 387 [M]+. Anal. Calcd for C23H21N3O3: C, 71.30; H, 5.46; N, 10.85. Found: C, 71.43; H, 5.38; N, 10.63. 80 Typical Experimental Procedure for the Synthesis of Poly(aldehydes) 13, 15, 17 and 23 To a stirred solution of 4-formylbenzoic acid (11) in ethanol (10 mL), KOH (3, 4, or 6 mmol) was added. The reaction mixture was stirred at room temperature for 10 min. The solvent was then removed in vacuo, and the remaining solid was triturated with dry diethyl ether, collected, and dried to give the corresponding potassium salts. A solution of the latter salts (3, 4, or 6 mmol) and the corresponding poly(bromo) compounds (1 mmol) in DMF (20 mL) was heated under reflux for 5 min during which time KBr was precipitated. The solvent was then removed in vacuo, and the remaining material was washed with water (50 mL) and crystallized from the proper solvents to give the corresponding poly(aldehydes). Compound 13: colorless crystals (butanol, 76%); mp >300 °C. IR (KBr): ν = 1714 (br, 2 CO) cm–1. 1H NMR (DMSO-d 6): δ = 5.46 (s, 6 H, 3-OCH2), 7.59 (s, 3 H, Ar-H), 7.98–8.17 (m, 12 H, Ar-H), 10.10 (s, 3 H, 3-CHO). 13C NMR (DMSO-d 6): δ = 66.1, 126.8, 129.5, 129.8, 134.1, 136.7, 139.1, 164.7, 192.7. MS (EI): m/z = 564 [M]+. Anal. Calcd for C33H24O9: C, 70.21; H, 4.29. Found: C, 70.18; H, 4.06. Compound 15: colorless crystals (dioxane, 83%); mp 200–204 °C. IR (KBr): ν = 1724, 1701 (2 CO) cm–1. 1H NMR (300 MHZ, DMSO-d 6): δ = 5.59 (s, 8 H, 4-OCH2), 7.81–8.05 (m, 18 H, Ar-H), 10.03 (s, 4 H, 4- CHO). MS (EI): m/z = 726 [M]+. Anal. Calcd for C42H30O12: C, 69.42; H, 4.16. Found: C, 69.53; H, 4.09. 81 Typical Experimental Procedure for the Synthesis of the Polypodal Compounds 9, 10, 18–21, 24, and 25 To a solution of the appropriate poly(aldehydes) (1 mmol) in DMF (10 mL), dimedone (2, 3, 4, or 6 mmol), aminobenzimidazole (3, 3, 4, or 6 mmol), and ZnO nanocatalyst (10 mol%) were added. The reaction mixture was heated at reflux for 1 h (method A) or irradiated in a focused microwave reactor for 15 min at 160 °C (250 W; method B). The crude solid was isolated and recrystallized from DMF/ethanol. Compound 9: pale yellow crystals, (method A, 85%; method B, 88%); mp >300 °C. 1H NMR (DMSO-d 6): δ = 0.93 (s, 9 H, 3 CH3), 1.05 (s, 9 H, 3 CH3), 2.02–2.27 (m, 6 H, 3 CH2), 2.54–2.59 (m, 6 H, 3 CH2), 4.95 (s, 6 H, 3-OCH2), 6.35 (s, 3 H, H12), 6.81–7.36 (m, 27 H, Ar-H), 11.02 (br, 3 H, NH). 13C NMR (DMSO-d 6): δ = 26.7, 28.6, 32.2, 50.0, 53.5, 69.0, 106.5, 110.0, 114.4, 116.9, 120.3, 121.7, 126.3, 128.1, 131.9, 134.0, 137.4, 141.9, 145.4, 150.0, 157.7, 192.5. Anal. Calcd for C75H69N9O6: C, 75.54; H, 5.83; N, 10.57. Found: C, 75.43; H, 5.77; N, 10.50. Compound 10: pale yellow crystals, (method A, 89%; method B, 89%); mp >300 °C. IR (KBr): ν = 3230 (NH), 1722, 1647 (2CO) cm–1. 1H NMR (DMSO-d 6): δ = 0.90 (s, 9 H, 3 CH3), 1.05 (s, 9 H, 3 CH3), 2.07–2.28 (m, 6 H, 3 CH2), 2.55–2.61 (m, 6 H, 3 CH2), 5.27 (s, 6 H, 3-OCH2), 6.52 (s, 3 H, H12), 6.92–7.85 (m, 27 H, Ar-H),11. 2 (br, 3 H, NH). 13C NMR (DMSO-d 6) : δ = 26.5, 28.5, 32.1, 49.8, 53.9, 65.6, 105.5, 109.7, 116.9, 120.4, 121.8, 126.7, 127.3, 128.7, 129.2, 131.7, 136.7, 141.8, 145.1, 146.5, 150.5, 164.9, 192.4. Anal. Calcd for C78H69N9O9: C, 73.39; H, 5.45; N, 9.88. Found: C, 73.51; H, 5.61; N, 9.92. 82 The IR spectra were recorded on potassium bromide disks on a PyeUnicam SP3-300 and Shimadzu FTIR 8101 PC infrared spectrophotometer. The 1H NMR and 13C NMR spectra were determined on a Varian Mercury VX 300 NMR spectrometer using TMS as an internal standard and DMSO-d 6 as a solvent. Mass spectra were measured on a GCMSQP1000 EX spectrometer at 70 eV. Elemental analyses were carried out at the Microanalytical Center of Cairo University, Giza, Egypt. ZnO NPs were used as purchased from Sigma-Aldrich. Characterization of ZnO NPs was provided as Supplementary Data. Zusatzmaterial Zusatzmaterial Supporting Information (PDF)
