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Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol

An iron-catalyzed aminoalcohol, a technology for catalyzing aminoalcohols, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., to achieve mild reaction conditions, good applicability, and easy operation. Effect

Inactive Publication Date: 2019-05-10
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method of synthesizing pyrroline through the reaction of amino alcohol and allyl alcohol, transition metal iron-catalyzed dehydrogenation coupling and carbon-carbon bond cleavage has not been reported yet.

Method used

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  • Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol
  • Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol
  • Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 2-(4'-methylphenyl)-1-pyrroline with the following structural formula

[0028]

[0029] Mix 24μL (0.0225mmol) sodium triethylborate with 5.3mg (0.0075mmol) [(Cy-PN H P)Fe(CO)(Br) 2 ], 1.5mL toluene was added to the reaction tube, mixed and stirred for 10 minutes, then 37.75mg (0.25mmol) 2-amino-1-(4-methylphenyl) ethanol, 34μL (0.5mmol) allyl alcohol, 48mg (0.375mmol) Potassium tert-butoxide, stirred and reacted at 120°C for 12 hours under the protection of argon, cooled to room temperature after the reaction, transferred with dichloromethane, dichloromethane and toluene were removed by distillation under reduced pressure, and purified with petroleum ether and ethyl acetate The volume ratio of the ester is 5:1 mixed solution as the eluent, and the product is separated by flash column chromatography to obtain 2-(4'-methylphenyl)-1-pyrroline with a yield of 73%, characterization data for: 1 H NMR (400MHz, CDCl 3 ):δ(ppm)7.74-7.72(d,2H),7.26-7.20(m,2H...

Embodiment 2

[0031] Preparation of 2-(benzo[d][1,3]dioxolyl)-1-pyrroline with the following structural formula

[0032]

[0033] In this example, the 2-amino-1-(4-methyl phenyl) ethanol, other steps are identical with embodiment 1, obtain 2-(benzo[d][1,3]dioxolyl)-1-pyrroline, its productive rate is 51%, characterization The data is: 1 H NMR (400MHz, CDCl 3 ): δ(ppm)7.43-7.42(d,1H),7.29-7.27(d,2H),6.83-6.81(d,1H),5.99(s,2H),4.04-4.01(t,2H),2.91 -2.86(t,2H),2.06-1.98(m,2H); 13 C NMR (100MHz, CDCl 3 ): δ (ppm) 172.5, 149.5, 148.0, 129.4, 122.7, 108.0, 107.5, 101.5, 61.4, 35.1, 22.9; HRMS (ESI + ) m / z C 10 h 11 N[M+H] + : The experimental value is 190.0868, and the theoretical value is 190.0859.

Embodiment 3

[0035] Preparation of 2-(4'-chlorophenyl)-1-pyrroline with the following structural formula

[0036]

[0037] In this example, the 2-amino-1-(4-methylphenyl)ethanol in Example 1 is replaced with equimolar 2-amino-1-(4-chlorophenyl)ethanol, and the other steps are the same as in Example 1 Identical, obtain 2-(4'-chlorophenyl)-1-pyrroline, its yield rate is 67%, and characteristic data is: 1 H NMR (400MHz, CDCl 3 ):δ(ppm)7.77-7.75(d,2H),7.38-7.36(m,2H),4.07-4.03(m,2H),2.93-2.88(m,2H),2.07-2.00(m,2H) ; 13 C NMR (100MHz, CDCl 3 ): δ (ppm) 172.3, 136.4, 133.2, 129.0, 128.8, 61.7, 35.0, 22.8; HRMS (ESI + )m / zC 10 h 11 N[M+H] + : The experimental value is 180.0588, and the theoretical value is 180.0580.

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Abstract

The invention discloses a method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol. In the atmosphere of inert gas, the amino alcohol and the enol serve as raw materials, potassium tert-butoxide is used as alkali, a series of pyrroline compounds are synthesized through the dehydrogenation coupling of low-cost transitional metal iron-catalyzed amino alcohol and theenol and the fracture of carbon-carbon bonds, the system is simple, the operation is simple and convenient, the reaction conditions are mild, and the reaction substrate has good applicability.

Description

technical field [0001] The invention belongs to the technical field of synthesizing pyrroline and its derivatives, and specifically relates to the synthesis of a series of pyrroline and its derivatives through the dehydrogenation coupling of amino alcohols and enols under the catalyst conditions of transition metal iron and the cleavage of carbon-carbon bonds. way of things. Background technique [0002] Pyrroline and its derivatives have proven to be valuable intermediates and multifunctional N-heterocyclic compounds. Due to its potential antibacterial, anti-inflammatory, anti-tumor, herbicidal and other biological activities, it has high application value in the field of pharmaceutical and pesticide production. [0003] The synthesis method of pyrroline includes the reaction of N-vinyllactam, lactim ether, 4-halonitrile and N-(trimethylsilyl)lactam with organometallic reagents (including alkyllithium and magnesium halide, etc.). In addition, tertiary phosphine can also b...

Claims

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Application Information

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IPC IPC(8): C07D207/20C07D405/04B01J31/24
Inventor 王超崔素雅马威肖建良
Owner SHAANXI NORMAL UNIV
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