A kind of preparation method of indolo[2,1-a]phthalazine derivative

A derivative, indole technology, applied in the field of indolo[2], can solve the problems of poor generality of synthetic substrates, few reaction selection sites, harsh reaction conditions, etc. Handling easy effects

Active Publication Date: 2021-03-23
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the synthetic substrates of pyrrolo[1,2-a]pyridazine derivatives have poor universality, few reaction sites and low yields.
In addition, the synthesis of pyridazino[1,6-a]indole derivatives is often carried out at low temperature (-78°C), and the reaction conditions are harsh

Method used

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  • A kind of preparation method of indolo[2,1-a]phthalazine derivative
  • A kind of preparation method of indolo[2,1-a]phthalazine derivative
  • A kind of preparation method of indolo[2,1-a]phthalazine derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of 12-phenylindolo[2,1-a]phthalazine:

[0024]

[0025] At room temperature, add 0.2 mmol of 2-(phenylethynyl) benzaldehyde and 0.4 mmol of phenylhydrazine to a reaction tube containing 1 mL of N,N-dimethylacetamide for 0.5 h, then add 0.1 mmol of DABCO (Triethylenediamine), 1mL N,N-dimethylacetamide, placed in an oil bath at 100°C, reacted for 15h, removed the heat source from the reaction, and cooled to room temperature. The reaction solution was extracted with water / ethyl acetate (50 mL / 50 mL), the collected organic phase was concentrated, and purified by column chromatography to obtain 46.1 mg of the target product with a yield of 78%. The compound is characterized as follows: 1 H NMR (400MHz, CDCl 3 )δ 8.27 (s, 1H), 8.18-8.13 (m, 1H), 7.87 (dd, J=6.9, 2.2Hz, 1H), 7.67-7.59 (m, 4H), 7.58-7.52 (m, 2H), 7.49-7.38(m, 4H), 7.34(ddd, J=7.9, 6.8, 1.1Hz, 1H); 13 C NMR (101MHz, CDCl 3 )δ 141.2, 135.1, 132.1, 131.5, 130.9, 130.9, 128.9, 128.4, 127.7, 127....

Embodiment 2

[0027] Preparation of 3-methoxy-12-phenylindolo[2,1-a]phthalazine:

[0028]

[0029] Under air atmosphere at room temperature, add 0.2 mmol of 5-methoxy-2-(phenylethynyl) benzaldehyde and 0.4 mmol of phenylhydrazine to a reaction tube containing 1 mL of NN-dimethylacetamide and react for 0.5 h , and then added 0.1 mmol DABCO (triethylenediamine), 1 mL N, N-dimethylacetamide, placed in an oil bath at 100 ° C, reacted for 15 h, removed the heat source from the reaction, and cooled to room temperature. The reaction solution was extracted with water / ethyl acetate (50 mL / 50 mL), the collected organic phase was concentrated, and purified by column chromatography to obtain 43.5 mg of the target product with a yield of 67%. The compound is characterized as follows: 1 H NMR (400MHz, CDCl 3 ): δ 8.26(s, 1H), 8.17(d, J=8.3Hz, 1H), 7.85(d, J=8.9Hz, 1H), 7.70-7.64(m, 3H), 7.58(t, J=7.6 Hz, 2H), 7.53-7.42(m, 2H), 7.37(ddd, J=7.9, 6.9, 1.1Hz, 1H), 7.12(d, J=2.7Hz, 1H), 7.06(dd, J=8.9, ...

Embodiment 3

[0031] Preparation of 3-chloro-12-phenylindolo[2,1-a]phthalazine:

[0032]

[0033] Under air atmosphere at room temperature, add 0.2mmol of 5-chloro-2-(phenylethynyl)benzaldehyde and 0.4mmol of phenylhydrazine to a reaction tube containing 1mL of N,N-dimethylacetamide and react for 0.5h , and then added 0.1 mmol DABCO (triethylenediamine), 1 mL N, N-dimethylacetamide, placed in an oil bath at 100 ° C, reacted for 15 h, removed the heat source from the reaction, and cooled to room temperature. The reaction solution was extracted with water / ethyl acetate (50mL / 50mL), the collected organic phase was concentrated, and purified by column chromatography to obtain 44.7 mg of the target product with a yield of 68%. The compound is characterized as follows: 1 H NMR (400MHz, CDCl 3 ): δ 8.21 (s, 1H), 8.17 (d, J = 8.2Hz, 1H), 7.82 (d, J = 8.7Hz, 1H), 7.69-7.65 (m, 2H), 7.64-7.56 (m, 4H ), 7.54-7.46 (m, 2H), 7.42-7.37 (m, 2H); 13 C NMR (101MHz, CDCl 3 ): δ 139.7, 134.8, 133.3, 13...

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Abstract

The invention discloses a preparation method of an indole[2,1-a]phthalazine derivative. According to the preparation method of the indole[2,1-a]phthalazine derivative, the indole[2,1-a]phthalazine derivative which cannot be synthesized by other methods is firstly and directly synthesized by a cascade reaction through relatively simple raw materials without the need to use a precious metal catalystand add an oxidizing agent, the reaction raw materials are easy to obtain, the yield is high, the reaction condition is mild, the reaction time is short, the substrate range is wide, and the post-treatment is simple and green.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of indolo[2,1-a]phthalazine derivatives. Background technique [0002] Indolophthalazine derivatives are a class of widely used intermediates in organic synthesis, and have important application values ​​in natural products, pharmaceutical production, and organic synthesis. Therefore, the study of new synthesis methods of multi-substituted indolophthalazine derivatives has important application value and has attracted the attention of researchers in related fields. [0003] At present, there are no reports on the synthesis of indolo[2,1-a]phthalazine derivatives, but only a few related to its analogs pyrrolo[1,2-a]pyridazine or pyridazino[1,6-a ] Synthetic method of indole derivatives. Among them, the synthetic substrates of pyrrolo[1,2-a]pyridazine derivatives have poor universality, few reaction sites and low yields. In addition, th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 王连会施兆江崔秀灵
Owner HUAQIAO UNIVERSITY
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