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Preparation method of 3-sulfuryl quinoline compound

A technology of sulfone quinoline and compounds, which is applied in the field of preparation of 3-sulfone quinoline compounds, can solve the problems that are not suitable for large-scale industrial application and will cause problems, and achieve strong substrate designability and simple preparation process , strong practical effect

Active Publication Date: 2020-11-24
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method needs to use a strong oxidant, and will produce equivalent salt and other by-products, which is not suitable for industrial large-scale application, and also poses a great pressure on environmental protection

Method used

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  • Preparation method of 3-sulfuryl quinoline compound
  • Preparation method of 3-sulfuryl quinoline compound
  • Preparation method of 3-sulfuryl quinoline compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of preparation method of 3-sulfonyl quinoline compound, with diiodine pentoxide as initiator, peroxy tert-butanol as oxidant, by mixing alkynyl imine compound and sulfonyl hydrazide compound, cyclization reaction occurs, 3-sulfonyl quinoline compounds were obtained.

[0036] The structure of the 3-sulfone quinoline compound is shown in formula I; the structure of the alkynyl imine compound is shown in formula II: the structure of the sulfonyl hydrazide compound is shown in formula III:

[0037]

[0038] In the formula:

[0039] R 1 One selected from hydrogen, p-chloro or p-methyl;

[0040] R 2 One selected from phenyl, thienyl or cyclopropyl;

[0041] R 3 One selected from phenyl, tert-butyl or hydrogen;

[0042] R 4 One selected from phenyl or thienyl.

[0043] Described preparation method comprises the steps:

[0044] (1) At a certain temperature, add an alkynyl imine compound, a sulfonyl hydrazide compound and an organic solvent into the test tube ...

Embodiment 2

[0057] Take a 25mL test tube reactor, add 0.5mmol alkynyl imine, 0.6mmol sulfonyl hydrazide and 5mL acetonitrile. At 70° C., 0.5 mmol of diiodine pentoxide and 2.5 mmol of tert-butanol peroxide were added to the above reaction system, and stirred for 8 hours. The progress of the reaction was detected by TLC (petroleum ether: ethyl acetate = 3:1). After the reaction is complete, add 20 mL of saturated ammonium chloride aqueous solution to quench the reaction, separate the organic phase, extract the aqueous phase three times with ether (50 mL each time), combine the organic phases, dry over anhydrous sodium sulfate, remove the solvent, and use petroleum ether: ethyl acetate Esters=3:1 eluent column chromatography, to obtain a white solid, which is 3-sulfone quinoline compounds, yield: 74%, its structural formula is as follows:

[0058]

[0059] Its NMR ( 1 HNMR and 13 C NMR) detection data are:

[0060] 1 H NMR (500MHz, CDCl 3 )δ8.19(d,J=8.0Hz,1H),8.05–7.94(m,5H),7.76–7...

Embodiment 3

[0063] Take a 25mL test tube reactor, add 0.5mmol alkynyl imine, 0.6mmol sulfonyl hydrazide and 5mL acetonitrile. At 70° C., 0.5 mmol of diiodine pentoxide and 2.5 mmol of tert-butanol peroxide were added to the above reaction system, and stirred for 8 hours. The progress of the reaction was detected by TLC (petroleum ether: ethyl acetate = 3:1). After the reaction is complete, add 20 mL of saturated ammonium chloride aqueous solution to quench the reaction, separate the organic phase, extract the aqueous phase three times with ether (50 mL each time), combine the organic phases, dry over anhydrous sodium sulfate, remove the solvent, and use petroleum ether: ethyl acetate Esters=3:1 eluent column chromatography, to obtain a white solid, which is 3-sulfone quinoline compounds, yield: 71%, its structural formula is as follows:

[0064]

[0065] Its NMR ( 1 HNMR and 13 C NMR) detection data are:

[0066] 1 H NMR (500MHz, CDCl 3 )δ8.09(d,J=9.0Hz,1H),7.95–7.84(m,5H),7.76–7...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of a 3-sulfuryl quinoline compound. The preparation method comprises the following steps: by taking iodine pentoxide as an initiator and tert-butyl hydroperoxide as an oxidant, mixing an alkynyl imine compound with a sulfohydrazide compound, and carrying out cyclization reaction to obtain the 3-sulfuryl quinoline compound. The preparation method of the 3-sulfuryl quinoline compound has the characteristics of easiness in operation, simplicity and convenience in post-treatment, strong substrate designability and the like, can be used for designing and synthesizing a compound with a required structure according to actual needs, and is strong in practicability. Meanwhile, the compound prepared by the method is good in physiological activity, can be used as a raw material for synthesizing a series of heterocyclic compounds, and has a high economic value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-sulfone quinoline compounds. Background technique [0002] Quinolines are an important intermediate in organic synthesis and one of the common structural units in natural products. They have a variety of important physiological activities and have great development and application value in the fields of biotechnology, medicine and pesticide development (ref. I: Metal-free domino one-pot protocols for quinoline synthesis, J.B.Bharate, R.A.Vishwakarma and S.B.Bharate, RSC Adv.2015, 5, 42020-42053; Literature II: Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides with Sodium sulfate, B. Du, P. Qian, Y. Wang, H. Mei, J. Han, Y. Pan, Org. Lett. 2016, 18, 4144-4147). The preparation method of a class of 3-sulfone quinoline compounds is rarely reported in the literature. [0003] At present, the known method of synthesizing 3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/36C07D409/04C07D409/12
CPCC07D215/36C07D409/04C07D409/12Y02A50/30
Inventor 单营营苏蕾赵子涵陈佃鹏
Owner QUFU NORMAL UNIV
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