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Tactico derivatives and their preparation methods

A derivative, triazole technology, applied in the field of triazole derivatives and its preparation, can solve the problems of narrow substrate range, narrow reaction substrate range, high reaction temperature, etc., and achieve reaction economy and substrate universality The effect of wide and easy-to-obtain raw materials

Active Publication Date: 2020-04-17
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) Michael J. Stocks and others reported the preparation of triazole derivatives from primary amines, amide diacetal derivatives, and hydrazide derivatives, but multi-step reactions are required and the scope of reaction substrates is narrow (see: Michael J. Stocks ; Org. Lett. 2004, 6 , 2969);
[0004] (2) Hideko Nagasawa et al. reported the preparation of triazole derivatives from amidine hydrochloride derivatives and organic nitriles, but the reaction temperature was high and the substrate range was narrow (see: Hideko Nagasawa; J. Am. Chem. Soc. 2009, 131 ,15080);

Method used

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  • Tactico derivatives and their preparation methods
  • Tactico derivatives and their preparation methods
  • Tactico derivatives and their preparation methods

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] The reaction flask was filled with compound 1p (0.2 mmol, 50.6 mg), CuBr (0.04 mmol, 5.8 mg), Li 2 CO 3 (14.8 mmol,), compound 3a (0.5 mL), compound 2a (0.6 mmol, 72.1 mg). Then the system was magnetically stirred and reacted at 40°C in the air for 1 hour, quenched with ethyl acetate, removed the solvent with a rotary evaporator, adsorbed on silica gel, and the product 4p was obtained by simple column chromatography with a yield of 63 %. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0040] 1 H NMR (400 MHz, CDCl 3 ) δ 7.39 – 7.30 (m, 2H), 7.28 – 7.23 (m, 1H),4.33 (q, J = 8.0 Hz, 2H), 2.56 (s, 3H), 2.08 (s, 3H), 1.28 (t, J = 8.0 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 161.96, 156.60, 146.00, 137.50, 135.30,131.80, 130.53, 129.05, 127.32, 62.43, 17.68, 13.95, 13.82. HRMS (ESI-TOF): Anal. Calcd. For C 13 h 14 ClN 3 o 2 +Na ...

Embodiment 2

[0042]

[0043] The reaction flask was filled with compound 1q (0.2 mmol, 52.9 mg), CuBr (0.04 mmol, 5.8 mg), Li 2 CO 3 (14.8 mmol,), compound 3a (0.5 mL), compound 2a (0.6 mmol, 72.1 mg). Then the system was magnetically stirred and reacted at 40°C in the air for 1 hour, quenched with ethyl acetate, removed the solvent with a rotary evaporator, adsorbed on silica gel, and the product 4q was obtained by simple column chromatography with a yield of 41 %. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0044] 1 H NMR (400 MHz, CDCl 3 ) δ 8.15 (d, J = 2.2 Hz, 1H), 7.64 (dd, J = 8.2,2.2 Hz, 1H), 7.49 (d, J = 8.3 Hz, 1H), 4.41 (q, J= 8.0 Hz, 2H), 2.70 (s,3H), 2.52 (s, 3H), 1.38 (t, J = 8.0 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ161.58, 157.13, 148.59, 144.79, 136.25, 135.09, 133.11, 129.91, 122.26,62.88, 20.41, 13.94, 13.73. HRMS (ESI-TOF)...

Embodiment 3

[0046]

[0047] The reaction flask was filled with compound 1r (0.2 mmol, 55.6 mg), CuBr (0.04 mmol, 5.8 mg), Li 2 CO 3 (14.8 mmol,), compound 3a (0.5 mL), compound 2a (0.6 mmol, 72.1 mg). Then the system was magnetically stirred and reacted at 40°C in the air for 1 hour, quenched with ethyl acetate, removed the solvent with a rotary evaporator, adsorbed on silica gel, and the product 4r was obtained by simple column chromatography with a yield of 39 %. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0048] 1 H NMR (400 MHz, CDCl 3 ) δ 8.03 (d, J = 2.3 Hz, 1H), 7.48 (dd, J = 8.2,2.4 Hz, 1H), 7.38 (d, J = 8.2 Hz, 1H), 4.38 (q, J = 8.0 Hz, 2H), 3.90 (s,3H), 2.69 (s, 3H), 2.52 (s, 3H), 1.35 (t, J = 8.0 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 166.47, 161.15, 157.22, 144.77, 142.09, 135.57, 132.16, 129.86, 128.82, 127.87, 62.59, 52.04, 21...

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Abstract

The invention discloses a triazole derivative and a preparation method thereof. According to the preparation method, aryl diazonium fluoroborate, a diazoester derivative and organic nitrile are takenas reaction substrates, transition metal is taken as a catalyst, inorganic alkali is taken as an additive, and the triazole derivative is prepared by virtue of cyclization reaction. The preparation method has the characteristics that the reaction is relatively economical, the substrates are relatively wide in universality, the later-period functionalization is relatively easily realized, reactionconditions are mild, the reaction can be carried out in air, the dose of a catalyst is low, the post-treatment is simple and convenient, and the purification and industrial utilization of a product are promoted; and meanwhile, the raw materials including reactants and catalysts adopted in the preparation method are cheap and easily available, the reaction constitution is reasonable, a ligand is not required, reaction steps are few, the relatively high yield can be realized only through one-step reaction, and the preparation method is accordant with the requirements and directions of current environment-friendly chemistry and pharmaceutical chemistry and is suitable for screening high-activity triazole derivative drugs.

Description

technical field [0001] The invention relates to a triazole derivative and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Triazole derivatives, as a very valuable five-membered nitrogen-containing heterocyclic skeleton, widely exist in many functional molecules and are used in organic catalysis, material science and other fields. In addition, the triazole derivative skeleton also appears in many biologically active molecules, and has important uses in the pharmaceutical industry and pesticides. At present, the method for preparing triazole derivatives has the disadvantages of many reaction steps, complicated preparation of raw materials, complicated reaction conditions, and narrow substrate scope. For example: [0003] (1) Michael J. Stocks and others reported the preparation of triazole derivatives from primary amines, amide diacetal derivatives, and hydrazide derivatives, but multi-step reactions are requ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/10B01J27/122
CPCB01J27/122C07D249/10
Inventor 李海燕李辉煌王亚雄万小兵
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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