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A compound and nitrile technology, applied in the field of preparation of nitrile compounds and one-pot synthesis of heterocyclic compounds, can solve the problems of complicated operation, poor selectivity, long synthesis steps, etc.
Active Publication Date: 2013-03-13
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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Problems solved by technology
However, these methods have many disadvantages, such as 1) the synthesis steps are too long, and each step needs to be purified; 2) the operation is complicated, high temperature and high pressure; 3) the yield is low, the selectivity is poor, and there are many by-products; Large environmental pollution; 4) Long reaction time and low efficiency
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Embodiment 1
[0084] Embodiment 1. Preparation and characterization of benzonitrile
[0085]
[0086] Add 9.5mg (0.05mmol) of cuprous iodide, 7.8mg (0.05mmol) of bipyridine, and 7.8mg (0.05mmol) of tetramethylpiperidine oxide into a dry 10mL schlenk bottle, 2mL of anhydrous EtOH, oxygen replacement Three times, slowly add 1.0mmol benzyl alcohol, 150uL ammonia water (2.0mmol, 2.0eq), stir at room temperature for 24h, monitor the reaction by TLC, after the reaction is completed, separate by column chromatography to obtain the target product, a colorless liquid, with a yield of 97%. 1 H NMR (400MHz, CDCl 3 )δ7.68 7.55(m,3H),7.47(t,J=7.7Hz,2H); 13 C NMR (100MHz, CDCl 3 )δ132.82,132.16,129.16,118.86,112.43; MS(70eV):m / z(%)103.1(M+,100).
Embodiment 2
[0087] Preparation and characterization of embodiment 2.2-methoxybenzonitrile
[0088]
[0089] Using 2-methoxybenzyl alcohol (1.0 mmol), the title compound was prepared by a method similar to that described in Example 1 as a yellow oily liquid with a yield of 99%. 1 H NMR (400MHz, CDCl 3 )δ7.567.51(m,2H),7.01 6.96(m,2H),3.92(s,3H); 13 C NMR (100MHz, CDCl 3 )δ161.17, 134.41, 133.66, 120.72, 116.49, 111.28, 101.64, 56.96; MS (70eV): m / z (%) 133.1 (M + ,100).
Embodiment 3
[0090] Preparation and characterization of embodiment 3.3-methoxybenzonitrile
[0091]
[0092] Using 3-methoxybenzyl alcohol (1.0 mmol), the title compound was prepared by a method similar to that described in Example 1 as a colorless oily liquid with a yield of 90%. 1 H NMR (400MHz, CDCl 3 )δ7.417.37(m,1H),7.27 7.25(m,1H),7.16 7.14(m,2H),3.85(s,3H); 13 C NMR (100MHz, CDCl 3 )δ159.62, 130.35, 124.50, 119.33, 118.73, 116.85, 113.18, 55.59; MS (70eV): m / z (%) 133.1 (M + ,100).
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Abstract
The invention discloses a method for effectively synthesizing a nitrile compound by reacting a copper salt, a ligand and a co-catalyst, a final oxidant such as with ammonia water under the mild condition in an alcohol and synthesizing multiple heterocyclic compounds with a one-pot method. In the method, the substrate adaptability is wide, the reaction time is short, the yield is high and the atom economy is high. Use of severe conditions, such as high temperature and high pressure and toxic starting materials is avoided; and the preparation method is simple in operation steps and less in corrosion on instruments, generates less waste gas, waste water and industrial residue, and is beneficial to further popularization and application, and industrial production.
Description
technical field [0001] The application relates to a nitrile compound and a preparation method for one-pot synthesis of a heterocyclic compound. Specifically, the application relates to a method for efficiently synthesizing nitrile compounds and one-pot synthesizing heterocyclic compounds with alcohol and ammonia under the catalysis of copper salts, ligands, and co-catalysts, and final oxidants such as oxygen. Background technique [0002] Nitrile compounds are an important building block for the synthesis of pharmaceutical intermediates and the preparation of functional materials. The classic methods for the synthesis of nitriles include the substitution of cyano groups with halogens, and the oxidation of ammonia, amides, and aldoximes. However, these methods have many disadvantages, such as 1) the synthesis steps are too long, and each step needs to be purified; 2) the operation is complicated, high temperature and high pressure; 3) the yield is low, the selectivity is poo...
Claims
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