Synthesis of indiacens A

A synthesis method and dropping technique, applied in organic chemistry and other directions, can solve the problems of poor stability and increase the difficulty of the reaction, and achieve the effects of less solvent consumption, easy operation and high yield.

Active Publication Date: 2021-09-17
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Enyne 10 is then reacted with trimethylaluminum and zirconocene dichloride to give allene 11 using three equivalents of the flammable hazard reagent trimethylaluminum and 0.25 equivalents of zirconocene dichloride reagent, and The product allene 11 is an unstable compound, which increases the difficulty of the reaction, and it needs to be put into the next Vilsmeier-Haack formylation reaction immediately. Due to the poor stability of the substrate 11, the yield of the formylation reaction, which should have a high yield, is only 58%.

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  • Synthesis of indiacens A
  • Synthesis of indiacens A
  • Synthesis of indiacens A

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Add 120mL of dry N,N-dimethylformamide into a 500mL three-neck round bottom flask and cool down to 0°C, slowly drop in 11mL (0.12mol) of phosphorus oxychloride under vigorous stirring, continue stirring for 5min, slowly drop in Dissolve 10g (0.048mol) of 4-bromoindole (purity: 95%) in 20g of dry N,N-dimethylformamide. After the dropwise addition, remove the cold bath and continue the reaction for 1h. At this time, the reaction solution becomes viscous Slowly drop 4.7M potassium hydroxide solution into the reaction suspension (the dropping rate is to maintain the reaction solution at 65-75°C, if the temperature is too high, it can be cooled in a water bath), and the reaction is continued for 6 hours after the addition is completed. Slowly add 20 mL of a saturated solution of sodium bicarbonate dropwise, continue stirring for 5 min, add ethyl acetate to dilute and extract, dry, and concentrate under reduced pressure to obtain 12 g of the crude 4-bromoindole-3-carbaldehyde;...

Embodiment 2

[0034] Add 120mL of dry N,N-dimethylformamide into a 500mL three-neck round bottom flask and cool down to 0°C, slowly drop in 11mL (0.12mol) of phosphorus oxychloride under vigorous stirring, continue stirring for 10min, slowly drop in Dissolve 10g (0.048mol) of 4-bromoindole (purity 96%) in 20g of dry N,N-dimethylformamide. After the dropwise addition, remove the cold bath and continue the reaction for 2h. At this time, the reaction solution becomes viscous Slowly drop into the reaction suspension solution dissolved in 4.7M sodium hydroxide solution (the dropping rate is to maintain the reaction solution at 65-75°C, if the temperature is too high, it can be cooled in a water bath), and continue the reaction after the dropwise addition 8h, slowly add 20mL of saturated sodium bicarbonate solution dropwise, continue to stir for 10min, add ethyl acetate to dilute, extract, dry, and concentrate under reduced pressure to obtain 12g of the crude 4-bromoindole-3-carbaldehyde;

[0035...

Embodiment 3

[0038] Add 120mL of dry N,N-dimethylformamide into a 500mL three-neck round bottom flask and cool down to 0°C, slowly drop in 11mL (0.12mol) of phosphorus oxychloride under vigorous stirring, continue stirring for 15min, slowly drop in Dissolve 10g (0.048mol) of 4-bromoindole (purity: 97%) in 20g of dry N,N-dimethylformamide. After the dropwise addition, remove the cold bath and continue the reaction for 3h. At this time, the reaction solution becomes viscous Slowly drop into the reaction suspension solution dissolved in 4.7M lithium hydroxide solution (the dropping rate is to maintain the reaction solution at 65-75°C, if the temperature is too high, it can be cooled in a water bath), and continue the reaction after the dropwise addition 10h, slowly add 20mL of saturated sodium bicarbonate solution dropwise, continue stirring for 15min, add ethyl acetate to dilute, extract, dry, and concentrate under reduced pressure to obtain 13g of the crude 4-bromoindole-3-carbaldehyde;

[...

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Abstract

The present invention provides a synthetic method of Indiacens A, relates to the field of organic synthesis, comprising the following steps: (1) synthesis of 4-bromoindole-3-formaldehyde; (2) purification of 4-bromoindole-3-formaldehyde; (3) Indiacens A is synthesized from 4-bromoindole-3-formaldehyde. The present invention has the advantages of cheap raw materials, mature reaction, short synthesis steps and high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of Indiacens A. Background technique [0002] In 2012, Indiacens A was isolated from a new type of myxobacteria by German scientist Heinrich Steinmetz. Biological activity tests showed that Indiaacens A had killing activity against Gram-positive bacteria, Gram-negative bacteria and the fungus Mucor permafrost. (J. Nat. Prod. 2012, 75, 1803-1805; DOI: org / 10.1021 / np300288b). In 1984, Masanori Somei and Yamada Fumio obtained Indiacens A as a by-product when completing (±)-Secoargoclavine (Chem.Pharm.Bull.1984,32,5064-5065; DOI: org / 10.1248 / cpb.32.5064) , synthetic route 1 such as figure 1 As shown, in this route, Masanori Somei and Yamada Fumio first prepared organic thallium compound 2 using indole-3-carboxaldehyde 1 as the starting material. In this step, 1.5 times the equivalent of highly toxic thallium trifluoroacetate reagent and Strong corrosive solvent ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 江世智雷婷陈紫瑞
Owner DALI UNIV
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