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Multi-substituted 2-pyrrole pyridine derivatives and preparation method thereof

A technology for pyrrole pyridine and derivatives, applied in the field of multi-substituted 2-pyrrole pyridine derivatives and its preparation, can solve the problems of difficult synthesis of multi-substituted 2-pyrrole pyridine derivatives, metal residues in products, toxicity of raw materials, etc., and achieve reaction Strong specificity, mild reaction conditions, and easy post-treatment

Active Publication Date: 2017-01-04
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many problems in these methods: 1) the above-mentioned methods all use pyridine or polysubstituted pyridines as raw materials, and the raw materials are highly toxic, and some polysubstituted pyridines are difficult to obtain; Metal residues, limited use in the pharmaceutical industry; 3) It is difficult to synthesize multi-substituted 2-pyrrole pyridine derivatives, especially highly selective synthesis of multi-substituted 2-pyrrole pyridine derivatives

Method used

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  • Multi-substituted 2-pyrrole pyridine derivatives and preparation method thereof
  • Multi-substituted 2-pyrrole pyridine derivatives and preparation method thereof
  • Multi-substituted 2-pyrrole pyridine derivatives and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Preparation of 2-(3-benzoyl-2-phenyl-4-methylpyrrole-1-)-4,6-diphenyl-3-methylpyridine

[0023]

[0024] Add 1,3-diphenyl-3-(prop-2-yn-1-amino)prop-2-en-1-one 0.5 mmol, potassium hydroxide 1 mmol, and acetonitrile 1.5 mL into a 10 mL reaction tube, set it to In an oil bath at 120°C, the reaction was carried out for 0.5h. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with ethyl acetate, washed with water three times, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 114.7 mg of the target product with a yield of 91%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.03(d,J=7.4Hz,2H),7.50-7.41(m,4H),7.24(dd,J=7.9,3.1Hz,2H),7.21-7.13(m,2H),7.03-6.84 (m, 9H), 6.82(d, J=7.4Hz, 1H), 2.43(s, 3H), 2.31(s, 3H), 1.41(s, 3H), 0.86(d, J=6.8Hz, 3H) . 13 C NMR (101MHz, CDCl3)δ196.0,154.0,153.3,151.3,140.4,139.,138.4...

Embodiment 2

[0026] Preparation of 2-(3-o-toluoyl-2-phenyl-4-methylpyrrole-1-)-4-o-tolyl-6-phenyl-3-methylpyridine

[0027]

[0028] Add 1-o-tolyl-3-phenyl-3-(prop-2-yn-1-amino)prop-2-en-1-one 0.5mmol, NaOH 1mmol, and acetonitrile 5mL into a 10mL reaction tube, set In an oil bath at 80 °C, the reaction was carried out for 0.5 h. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with ethyl acetate, washed with water three times, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 103.7 mg of the target product with a yield of 78%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.03(d,J=7.4Hz,2H),7.50-7.41(m,4H),7.24(dd,J=7.9,3.1Hz,2H),7.21-7.13(m,2H),7.03-6.84 (m, 9H), 6.82(d, J=7.4Hz, 1H), 2.43(s, 3H), 2.31(s, 3H), 1.41(s, 3H), 0.86(d, J=6.8Hz, 3H) ; 13 C NMR (101MHz, CDCl 3 )δ196.0,154.0,153.3,151.3,140.4,139.,138.4,138.1,13...

Embodiment 3

[0030] Preparation of 2-(3-p-Toluoyl-2-phenyl-4-methylpyrrole-1-)-4-p-tolyl-6-phenyl-3-methylpyridine

[0031]

[0032] Add 1-p-tolyl-3-phenyl-3-(prop-2-yn-1-amino)prop-2-en-1-one 0.5mmol, potassium tert-butoxide 1mmol, dimethyl sulfoxide 3mL to 10mL The reaction tube was placed in an oil bath at 50 °C and reacted for 1 h. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with ethyl acetate, washed with water three times, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 66.2 mg of the target product with a yield of 49%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.02(d,J=7.7Hz,2H),7.60(d,J=7.5Hz,3H),7.46(dt,J=14.4,7.1Hz,3H),7.17(d,J=7.9Hz, 2H), 7.06–6.88(m, 10H), 2.36(s, 3H), 2.27(s, 3H), 2.23(s, 3H), 1.59(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ1945,154.0,153.1,151.9,142.1,138.3,138.1,137.0,136.6,135.9,131.7,13...

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Abstract

The invention discloses a polysubstituted 2-pyrrolopyridine derivative. The derivative has a structure shown in a formula in the specification, wherein in the formula, R1, R2, R3, R4, R5, R6, R7 and R8 are selected from any one of hydrogen atoms, halogen atoms, alkyl, aryl, substituted aryl, acyl, amino, nitro and alkoxy. The invention also discloses a preparation method of the polysubstituted 2-pyrrolopyridine derivative. The polysubstituted 2-pyrrolopyridine derivative shown in the formula is obtained at high yield after completing heating reaction of N-propargyl enaminone in a solvent in the presence of appropriate alkali. The polysubstituted 2-pyrrolopyridine derivative and the preparation method have the beneficial effects that the reaction conditions are mild; the reaction time is short; the range of substrates is wide; the reaction specificity is strong; the yield is high; aftertreatment is simple and convenient to carry out.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a polysubstituted 2-pyrrole pyridine derivative and a preparation method thereof. Background technique [0002] Polysubstituted 2-pyrrole pyridine derivatives are a kind of organic synthesis intermediates with a wide range of uses, and have important application value in natural products, pharmaceutical production, organic synthesis, and materials science. Therefore, the research on new synthetic methods of polysubstituted 2-pyrrolepyridines has important application value and has attracted the attention of researchers in related fields. [0003] Traditional methods for synthesizing 2-pyrrolepyridine derivatives include the condensation reaction of 2-aminopyridine with 1,4-dicarbonyl compounds, and the copper-catalyzed coupling reaction of 2-halopyridine with amine compounds. But these methods all have many problems: 1) the above methods all use pyridine or multi-subst...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D409/14
CPCC07D401/04C07D409/14
Inventor 崔秀灵沈金海
Owner HUAQIAO UNIVERSITY
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