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Method for synthesizing tricyclic skeleton 2-pyridone and 2-pyridine imine compounds

A technology of pyridine imines and compounds, applied in the field of chemical synthesis, which can solve problems such as lack of synthesis methods, cumbersome operations, and complicated raw materials, and achieve the effects of no catalyst, high reaction yield, and easy-to-obtain raw materials

Pending Publication Date: 2021-09-21
XI AN JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, at present, the synthetic method of the 2-pyridone structure of the synthetic tricyclic skeleton is comparatively lacking, and the reported method usually has lengthy steps, complicated raw materials, cumbersome operations, harsh conditions or must use limitations such as catalysts (J.Org.Chem.1998 , 63, 44–54; Chem. Lett. 2009, 38, 1152–1153)

Method used

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  • Method for synthesizing tricyclic skeleton 2-pyridone and 2-pyridine imine compounds
  • Method for synthesizing tricyclic skeleton 2-pyridone and 2-pyridine imine compounds
  • Method for synthesizing tricyclic skeleton 2-pyridone and 2-pyridine imine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthetic tricyclic skeleton 2-pyridone compound

[0042]

[0043] Under nitrogen protection, DBN (0.2 mmol) was added to 2-cyano-3-phenylrokylene (0.4 mmol) of acetonitrile solution (1 mL), stirred at 120 ° C for 4 h, and after the reaction, cooled to room temperature; Filtration, methanol and n-hexane recrystallization (methanol: n-hexane = 1: 5), the product was 42.5 mg, the yield was 77%, the product was a yellow solid, melting point:> 289 ° C.

[0044] IR (ATR): 3675, 2973, 2794, 1700, 1614, 1557, 1538, 1495, 1440, 1392, 1366, 1308, 1273, 1188, 764, 740, 708, 670cm -1 .

[0045] 1 H NMR (400MHz, DMSO-D 6 : Δ7.54-7.39 (m, 5H), 3.83-3.75 (m, 2H), 3.72 (T, J = 8.3Hz, 2H), 3.32-3.29 (T, 2H), 2.76 (T, J = 8.2 Hz, 2H), 2.11-1.98 (m, 2H).

[0046] 13 C NMR (100MHz, DMSO-D 6 : δ161.2, 154.9, 150.2, 136.4, 129.4, 129.0, 128.3, 12.4, 102.4, 78.4, 51.8, 41.9, 38.1, 24.1, 19.6.

[0047] HRMS (ESI): M / Z: Calcd for C 17 Hide 16 N 3 O + [M + h] + : 278.1288; Found: 278...

Embodiment 2

[0048] Example 2: Synthetic tricyclic skeleton 2-pyridone compound

[0049]

[0050] Under nitrogen protection, DBN (0.2 mmol) was added to 2-cyano-3- (4-methoxyphenyl) acrylate (0.4 mmol) of acetonitrile solution (1 mL), stirred at 120 ° C for 4 h, After the reaction was completed, cooled to room temperature; concentrated, the column chromatography was separated (ethyl acetate: methanol = 5: 1), the product was 54.4 mg, the yield was 89%, the product was a yellow solid, the melting point was 224-225 ° C.

[0051]IR (ATR): 3547,2913,2190,1711,1614,1535,1510,1459,1418,1392,1372, 1307,1278,1252,1175,1117,1025,973,891,842,771,755,725,700,655cm -1 .

[0052] 1 H NMR (400MHz, CDCL 3 ): Δ7.38 (d, J = 8.6Hz, 2H), 6.93 (d, J = 8.6Hz, 2H), 3.95-3.89 (m, 2H), 3.83 (s, 3H), 3.73 (t, J = 8.4Hz, 2H), 3.33 (t, J = 5.8Hz, 2H), 2.89 (t, J = 8.4Hz, 2H), 2.16-2.07 (m, 2H).

[0053] 13 C NMR (100MHz, CDCL 3 ): Δ161.5,160.2,154.2,151.6,129.6,127.9,119.8,113.9,101.3,81.0,55.3,51.9,42.1,37.9,24.7,19....

Embodiment 3

[0055] Example 3: Synthesis of tricyclic skeleton 2- pyridones

[0056]

[0057] Under nitrogen, the DBN (0.2mmol) was added to 2-cyano-3- (4-chlorophenyl) (1 mL) and stirred for 4h at 120 ℃ ethyl acrylate (0.4 mmol) of acetonitrile, the reaction after cooling to room temperature; concentration, separation with column chromatography (ethyl acetate: methanol = 5: 1) to give product 35mg, 56% yield, the product as a yellow solid, mp 237-238 ℃.

[0058] IR (ATR): 3545,2912,2194,1617,1554,1534,1488,1406,1371,1307,1279, 1187,1151,1108,1089,1043,1009,977,891,833,768,754,700,651cm -1 .

[0059] 1 H NMR (400MHz, CDCL 3 ): Δ7.42-7.32 (m, 4H), 3.97-3.89 (m, 2H), 3.75 (t, J = 8.4Hz, 2H), 3.35 (t, J = 5.8Hz, 2H), 2.86 (t, J = 8.4Hz, 2H), 2.19-2.08 (m, 2H).

[0060] 13 C NMR (100MHz, CDCL 3 ): Δ161.2,154.3,150.7,135.3,134.1,129.5,128.8,119.3,101.4,80.8,51.9,42.1,37.9,24.3,19.8.

[0061] HRMS (ESI): m / z: calcd for C 17 Hide 15 CLN 3 O + [M + h] + : 312.0898; found: 312.0885.

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Abstract

The invention discloses a method for synthesizing tricyclic skeleton 2-pyridone and 2-pyridine imine compounds, which belongs to the technical field of chemical synthesis. The method comprises the steps that one molecule of DBN (1, 5-diazabicyclo [4.3.0] nonyl-5-ene) or DBU (1, 8-diazabicyclo [5.4.0] undec-7-ene) and one molecule of activated olefin, such asaryl methylene malononitrile and 2-cyano-3-aryl acrylate, are cyclized at room temperature or under a heating condition to form new carbon-carbon and nitrogen-carbon bonds, and the new carbon-carbon and nitrogen-carbon bonds areoxidized by another molecule of activated olefin to generate tricyclic skeleton 2-pyridone and 2-pyridine imine compounds. The operation is simple, the raw materials are easy to obtain, the conditions are mild, no catalyst is needed, the product is easy to separate and purify, the reaction yield is high, and the synthesis method is a great breakthrough of previous reactions and is expected to realize large-scale industrial production.

Description

Technical field [0001] The present invention belongs to the field of chemical synthesis, and more particularly to a method of synthesizing tricyclic skeleton 2-pyridone or 2-pyridine amine compound. Background technique [0002] 2-pyridone unit having a tricyclic skeleton has potential biologically active, which contains a significant efficacy of natural product (Chem.Pharm.Bull. 2005, 53, 67-71), and related reports also show The 2-pyridone of the tricyclic skeleton has excellent optical properties (int.ed.2015, 54, 14492-14497; Chem.commun.2014, 50, 5688-5690.). [0003] However, the synthesis method of 2-pyridone structure of the synthetic tricyclic skeleton is relatively lacking. The method of reporting is usually long, the raw material is complex, and the operation is cumbersome, and the need for harsh conditions or must use catalysts (j.chem.1998 63, 44-54; Chem.let.2009, 38, 1152-1153). Inventive content [0004] In order to overcome the disadvantages of the prior art, it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16
CPCC07D471/16
Inventor 徐四龙韩文丹张科强李志
Owner XI AN JIAOTONG UNIV
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