Preparation method of tryptopquinoline heterocyclic compound

A technology of heterocyclic compounds and quinoline, which is applied in the field of organic synthesis, can solve the problems of no chromonoquinoline heterocyclic compounds and cumbersome preparation methods, and achieve the effects of simple reaction, simple operation and low cost

Active Publication Date: 2019-06-28
SUZHOU UNIV
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Problems solved by technology

[0002] Chromone and quinoline heterocyclic compounds (12 H -chromeno[2,3- b ]quinolin-12-one and 6 H -chromeno[4,3- b ]quinolin-6-one) are two common chromonoquinoline heterocyclic structures, both of which are a pair of positional isomers; in the prior art, the preparation methods of chromonoquinoline heterocyclic c

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  • Preparation method of tryptopquinoline heterocyclic compound
  • Preparation method of tryptopquinoline heterocyclic compound
  • Preparation method of tryptopquinoline heterocyclic compound

Examples

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[0020] Example 1

[0021]

[0022] Add anthranilin 1 (60 mg, 0.5 mmol) and 4-hydroxycoumarin 2a (0.65 mmol) to a 15 mL test tube, then add DMI (0.75 mL); then heat the resulting mixture to 230 °C React for 1 hour; after the reaction is over, stop heating, cool to room temperature, add water and ethyl acetate, then wash the organic phase with water three times, combine the aqueous phases, extract the water with ethyl acetate, and finally combine the organic phases with anhydrous sulfuric acid After the sodium was dried, the solvent was evaporated under reduced pressure, and the residue was separated and purified by silica gel column chromatography to obtain products 3a and 4a, respectively, with a total yield of 69%, 3a:4a = 1.4:1. 3a: 1 H NMR (400 MHz, CDCl 3 ) δ: 9.29 (s, 1H), 8.41-8.30 (m, 1H), 8.16-8.03 (m, 2H), 7.92 (t, J =7.6 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.30 (d, J = 9.0 Hz, 1H), 7.15 (t, J =7.9 Hz, 1H); 13 C NMR (151 MHz, CDCl 3 ) δ: 177.02, 167.33 (d, J = 258.0 H...

Example Embodiment

[0023] Example 2

[0024]

[0025] Add anthranilin 1 (60 mg, 0.5 mmol) and 4-hydroxycoumarin 2a (0.05 mmol) to a 15 mL test tube, and then add DOA (0.75 mL). The reaction mixture was heated to 300 °C and reacted for 0.2 hours. Stop heating, cool to room temperature, add water and ethyl acetate. The organic phase was washed three times with water, the aqueous phases were combined, and the water was reversely extracted once with ethyl acetate. Finally, the organic phases were combined, dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent, and the residue was separated and purified by silica gel column chromatography to obtain the product 3a and 4a, the total yield is 55% (based on 4-hydroxycoumarin), 3a:4a = 1.2:1.

Example Embodiment

[0026] Example 3

[0027]

[0028] Add anthranilin 1 (60 mg, 0.5 mmol) and 4-hydroxycoumarin 2a (5 mmol) to a 15 mL test tube, and then add DMI (5 mL). The reaction mixture was heated to 150 °C for 5 hours. Stop heating, cool to room temperature, add water and ethyl acetate. The organic phase was washed three times with water, the aqueous phases were combined, and the water was reversely extracted once with ethyl acetate. Finally, the organic phases were combined, dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent, and the residue was separated and purified by silica gel column chromatography to obtain the product 3a and 4a, the total yield is 63%, 3a:4a = 1.3:1.

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Abstract

The invention discloses a method of preparing a tryptopquinoline heterocycle by carrying out a heating reaction on anthranil and 4-hydroxyl coumarin. The reaction comprises the following steps: dissolving anthranil and 4-hydroxyl coumarin in a solvent, and carrying out a reaction on the reaction mixture at 150-300 DEG C for 0.2-5 hours; and stopping heating, cooling the reactant to room temperature, adding water, extracting the reactant with a solvent, evaporating the reactant, carrying out purification by a column chromatography to obtain the tryptopquinoline heterocyclic compound. The preparation method is the reaction of anthranil and 4-hydroxyl coumarin in a thermal promoting condition. Catalysts and additives are not needed for the conversions, few byprodcuts are available, and the preparation method is a novel method of constructing the tryptopquinoline heterocyclic compound quickly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing chromonoquinoline heterocyclic compounds by reacting anthranilide and 4-hydroxycoumarin at high temperature. Background technique [0002] Chromone and quinoline heterocyclic compounds (12 H -chromeno[2,3- b ]quinolin-12-one and 6 H -chromeno[4,3- b ]quinolin-6-one) are two common chromonoquinoline heterocyclic structures, both of which are a pair of positional isomers; in the prior art, the preparation methods of chromonoquinoline heterocyclic compounds are mostly cumbersome . Anthranilic anhydride is a structure containing a 2,1-benzisoxazole heterocycle, which often participates in the reaction as a bifunctional reagent under the catalysis of various metals, but there is no preparation of chromonoquinoline heterocyclic compounds from anthranilic anhydride reports. Contents of the invention [0003] The technical problem to b...

Claims

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Application Information

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IPC IPC(8): C07D491/052
Inventor 张士磊毛玉健胡延维孙婉婉陈韶华
Owner SUZHOU UNIV
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