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Application of N-heterocyclic carbene-based mixed nickel (II) complex in reaction of synthesizing 2-linear alkylbenzothiazole compound

A technology for straight-chain alkylbenzenes and compounds, applied in the field of organic synthesis and preparation, can solve problems such as the inability to provide 2-linear alkylbenzothiazole compounds, achieve 100% atom economy, and catalysts are cheap and easy to obtain , the effect of mild reaction conditions

Active Publication Date: 2020-07-17
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Our research group has realized the hydroheteroarylation reaction of benzothiazole and arylethene by using mixed divalent nickel(II) complexes, but the reaction is used for arylethene substrates, so it cannot provide 2-direct Alkanyl benzothiazole compounds

Method used

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  • Application of N-heterocyclic carbene-based mixed nickel (II) complex in reaction of synthesizing 2-linear alkylbenzothiazole compound
  • Application of N-heterocyclic carbene-based mixed nickel (II) complex in reaction of synthesizing 2-linear alkylbenzothiazole compound
  • Application of N-heterocyclic carbene-based mixed nickel (II) complex in reaction of synthesizing 2-linear alkylbenzothiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 See CN108002966A, Catalyst nitrogen heterocyclic carbene mixed type nickel (II) complex Ni[P(OEt) 3 ][(RNCHCHNR)C]Br 2 The chemical structural formula of is as follows, for the following examples:

[0035]

[0036] R has the following structural formula:

[0037] .

Embodiment 2

[0038] Example 2 The divalent nickel (II) complex is used as a catalyst to catalyze the hydroheteroarylation reaction of 1-hexene and benzothiazole

[0039]

[0040] Under argon protection, catalyst (66 mg, 0.05 mmol, 10 mol%), magnesium chips (6.0 mg, 0.25 mmol), benzothiazole (54 μl, 0.5 mmol), 1 -Hexene (93 microliters, 0.75 mmol), tetrahydrofuran (1.5 milliliters) as solvent, at 60 o The reaction was carried out at C for 3 hours, and the reaction was terminated with water. The reaction product was extracted with ethyl acetate and purified by column chromatography (with a mixed solvent of ethyl acetate / petroleum ether volume ratio of 1:10 as the developing solvent), and the yield was 95%.

[0041] Dissolve the product in CDCl 3 Medium (about 0.4 mL), seal the tube, measure and characterize on a Unity Inova-400 NMR instrument at room temperature: 1 H NMR (400 MHz, CDCl 3 ): δ 7.98 (d, J = 8.3 Hz, 1H), 7.85 – 7.80 (m, 1H),7.45 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H), 7.38 –...

Embodiment 3

[0044] Example 3 The divalent nickel (II) complex is used as a catalyst to catalyze the hydroheteroarylation reaction of 1-heptene and benzothiazole

[0045] Under argon protection, catalyst (66 mg, 0.05 mmol, 10 mol%), magnesium chips (6.0 mg, 0.25 mmol), benzothiazole (54 μl, 0.5 mmol), 1 -heptene (106 microliters, 0.75 mmol), tetrahydrofuran (1.5 milliliters) as solvent, at 60 o The reaction was carried out at C for 3 hours, and the reaction was terminated with water. The reaction product was extracted with ethyl acetate, and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate / petroleum ether of 1:10 as the developing solvent), and the yield was 94%.

[0046] Dissolve the product in CDCl 3 Medium (about 0.4 mL), seal the tube, measure and characterize on a Unity Inova-400 NMR instrument at room temperature: 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d,J = 8.3 Hz, 1H), 7.87 – 7.80 (m, 1H),7.46 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H), 7.40 – 7...

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Abstract

The invention discloses an application of an N-heterocyclic carbinyl mixed nickel (II) complex in a reaction for synthesizing a 2-linear alkyl benzothiazole compound and a method for synthesizing the2-linear alkyl benzothiazole compound. The mixed nickel (II) complex containing Ni[P(OEt)3](RNCHCHNR)C]Br2[R is 2, 4, 6, 7, 8-tetramethyl-4-piperidinecarboxylic acid] is used as a catalyst, and the 2-linear alkyl benzothiazole compound is synthesized through a hydrogen heteroarylation reaction of aliphatic alpha-olefin and a benzothiazole compound in the presence of magnesium. Compared with the prior art, the invention avoids the use of expensive monovalent rhodium complexes, and provides a new method for preparing the 2-linear alkyl benzothiazole compound through the hydroheteroarylation reaction of the aliphatic alpha-olefin, which is realized by a divalent nickel catalyst.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis preparation, and in particular relates to a method for synthesizing 2-straight-chain alkylbenzothiazole compounds. Background technique [0002] Benzothiazole and its derivatives are a class of nitrogen- and sulfur-containing condensed heterocyclic compounds, which are widely used in the creation of pesticides and medicines as important lead frameworks with good biological activities. Industrially, these compounds are also used as rubber vulcanization accelerators and plastic dyes (see Dai, X. Q.; Zhu, Y. B.; Wang, Z. Y.; Wong, J. Q. Chin. J. Org. Chem. 2017, 37 , 1924). Among them, with the discovery of 2-substituted benzothiazole units in various bioactive molecules such as antibacterial, insecticidal, and anticancer, more and more attention has been paid to the development of their synthetic methods. However, the current methods for introducing a linear alkyl group at the 2-positio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/18C07D277/64
CPCB01J31/2273B01J31/185C07D277/64B01J2531/847B01J2531/0233B01J2531/0238B01J2231/32Y02P20/584
Inventor 孙宏枚水雨
Owner SUZHOU UNIV
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