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Preparation method of alpha-carbonyl amide derivatives

A technology of carbonyl amides and derivatives, applied in the field of organic synthesis, to achieve excellent yields, high reaction yields, and improved atom economy

Active Publication Date: 2018-12-28
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, most of the preparation methods for the synthesis of α-carbonyl amide derivatives are carried out by strategies such as small molecule coupling and metal catalyst oxidation (Chem. There are few reports on the preparation method of α-carbonyl amide derivatives by ringing and inserting oxygen atoms

Method used

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  • Preparation method of alpha-carbonyl amide derivatives
  • Preparation method of alpha-carbonyl amide derivatives
  • Preparation method of alpha-carbonyl amide derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: Preparation of N-cyclohexyl-2-oxo-2-phenylacetamide

[0021]

[0022] 1mmol N-cyclohexyl-2-phenylimidazol[1,2-a]pyridin-3-amine, 3mmol TsOH·H 2 O was added to a 10mL reaction tube with a stirring bar, 2.5mL of dichloroethane was added, and stirred. After stirring for 5 minutes, 1 mmol of iodobenzene acetate was added, stirred at room temperature, TLC followed the reaction, and the reaction was stopped after 1 hour. Analysis (petroleum ether: ethyl acetate = 5:1), precipitation, the target compound was obtained, the yield was 99.1%, light yellow solid; m.p.91-92°C; 1 H NMR (400MHz, Chloroform) δ8.33(d, J=7.3Hz, 2H), 7.62(t, J=7.4Hz, 1H), 7.47(t, J=7.7Hz, 2H), 6.97(s, 1H ),4.05–3.71(m,1H),2.07–1.93(m,2H),1.81–1.72(m,2H),1.70–1.63(m,1H),1.49–1.36(m,2H),1.33–1.21 (m,3H). 13 C NMR (101MHz, Chloroform) δ188.15, 160.86, 134.31, 133.47, 131.23, 128.46, 48.49, 32.73, 25.43, 24.76. HR-MS (ESI): Calculated for C 14 h 16 ClNO 2 [M+H] + :231.12593,found:231.1...

Embodiment 2

[0023] Embodiment 2: Preparation of 2-(4-chlorophenyl)-N-cyclohexyl-2-oxo-acetamide

[0024]

[0025]1mmol 2-(4-chlorophenyl)-N-cyclohexaneimidazol[1,2-a]pyridin-3-amine, 3mmol TsOH·H 2 O was added to a 10mL reaction tube with a stirring bar, 2.5mL of dichloroethane was added, and stirred. After stirring for 5 minutes, 1 mmol of iodobenzene acetate was added, stirred at room temperature, TLC followed the reaction, and the reaction was stopped after 1 hour. Analysis (petroleum ether: ethyl acetate = 5:1), precipitation, the target compound was obtained with a yield of 94.8%; white solid; m.p.90-91°C; 1 H NMR (500MHz, Chloroform-D) δ8.32 (d, J = 8.6Hz, 2H), 7.43 (d, J = 8.7Hz, 2H), 6.99 (s, 1H), 3.82 (m, 1H), 2.03 –1.92(m,2H),1.79–1.71(m,2H),1.73–1.56(m,1H),1.45–1.34(m,2H),1.24(m,3H). 13 C NMR (126MHz, DMSO-D6) δ189.91, 164.37, 139.99, 132.20, 132.02, 129.75, 48.31, 32.54, 25.57, 25.03. HR-MS (ESI): Calculated for C 14 h 16 ClNO 2 [M+H] + :266.09423,found:266.09384.

Embodiment 3

[0026] Embodiment 3: Preparation of N-cyclohexyl-2-(3-nitrophenyl)-2-oxo-acetamide

[0027]

[0028] 1mmol 2-(3-nitrophenyl)-N-cyclohexaneimidazol[1,2-a]pyridin-3-amine, 3mmol TsOH·H 2 O was added to a 10mL reaction tube with a stirring bar, 2.5mL of dichloroethane was added, and stirred. After stirring for 5 minutes, 1 mmol of iodobenzene acetate was added, stirred at room temperature, TLC followed the reaction, and the reaction was stopped after 1 hour. Analysis (petroleum ether: ethyl acetate = 5:1), precipitation, the target compound was obtained, the yield was 97.4%, white solid; m.p.91-92°C; 1 H NMR (500MHz, Chloroform-D) δ9.13–9.11(t,1H),8.66(tt,J=7.8,1.3Hz,1H),8.42(m,1H),7.65(t,J=8.0Hz, 1H),7.01(s,1H),1.45(s,9H). 13 C NMR (126MHz, Chloroform-D) δ186.25, 159.94, 148.21, 136.96, 134.72, 129.66, 128.21, 126.16, 52.07, 28.39. HR-MS (ESI): Calculated for C 12 h 14 N 2 o 4 [M+H] + :251.10.263,found:251.10222.

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Abstract

The invention discloses a preparation method of alpha-carbonyl amide derivatives. According to the method, pyridino-aminoimidazole compounds and water are subjected to ring-opening reaction under theaction of an oxidizing agent, meanwhile, oxygen atoms are inserted, and the alpha-carbonyl amide derivatives are prepared. The method is simple to operate, substrate universality is wide, metal catalysis is avoided in a reaction process, anhydrous and anaerobic conditions are not required, O atoms in the structure of the derivatives are derived from water, and by-products can be taken as pyridino-aminoimidazole raw materials for preparing the derivatives, thereby being recycled. The method further has the advantages of being high in yield and capable of being used for mass preparation of the alpha-carbonyl amide derivatives and preparation of part of the alpha-carbonyl amide derivatives which are relatively difficult to prepare with existing methods.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing amides and α-carbonyl amide derivatives through selective ring opening of pyridoimidazole amine compounds under different conditions. Background technique [0002] α-Carbonyl amide derivatives are a class of compounds with a wide range of biological activities. They are important fragments in the molecular structure of many drugs and are also important drug intermediates (Tetrahedron Letters, 2017, 58, 546–551; Chem.Eur . J. 2015, 21, 8033–8037). Therefore, the research on the synthesis method of α-carbonyl amide derivatives is a direction that people are more interested in, and a large number of literatures have reported α-carbonyl amide (Chemical Reviews 2016, 116, 3241; Organic Letters 2014, 16, 5772; Angewandte Chemie-International Edition2016,55,5327; Journal of the American Chemical Society 1985,107,3235-3245; Angewandte Chemie-Internation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07D213/61C07D307/54C07D333/24C07C235/78C07C235/74C07C235/84C07B43/06
CPCC07B43/06C07C231/10C07D213/61C07D307/54C07D333/24C07C2601/14C07C235/78C07C235/74C07C235/84
Inventor 吴剑徐方舟王艳艳寻曦炜黎泽莲罗德霞陈顺红薛伟
Owner GUIZHOU UNIV
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