Pyrazolo [5, 1-a] isoindole derivative as well as synthesis method and application thereof

By introducing a polarity reversal strategy of the cyano group, 2-(2-ethynylphenyl)acrylonitrile is reacted with a diazo compound in the presence of a catalyst and a base to construct a pyrazolo[5,1-a]isoindole derivative. This solves the problems of multiple steps and harsh conditions in existing synthetic methods, and realizes an efficient and universal pyrazolo[5,1-a]isoindole synthesis, which is suitable for drug molecule design.

CN122079996APending Publication Date: 2026-05-26LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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Patent Information

Application Number
CN202610079905.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2026-01-21
Publication Date
2026-05-26

AI Technical Summary

Technical Problem

Existing methods for synthesizing pyrazolo[5,1-a]isoindole compounds suffer from problems such as multi-step precursor synthesis, harsh reaction conditions, and limited substrate scope, which restricts their practicality.

Method used

By employing a polarity reversal strategy, a pyrazolo[5,1-a]isoindole derivative was constructed by introducing a cyano group into 1,5-enyne and reacting 2-(2-ethynylphenyl)acrylonitrile with a diazo compound under the conditions of a catalyst, base, and solvent, through a series of intermolecular [3+2] cycloaddition, intramolecular cycloaddition, and elimination reactions.

Benefits of technology

This study achieved efficient synthesis of pyrazolo[5,1-a]isoindole derivatives under mild conditions, with good synthetic yield, simple operation, readily available raw materials, and good substrate versatility, providing an effective strategy for drug design and synthesis.

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Abstract

The invention discloses a pyrazolo [5, 1-a] isoindole derivative as well as a synthesis method and application thereof, and belongs to the technical field of organic chemical synthesis. The invention solves the problems of harsh reaction conditions, limited substrate range and the like of continuous multi-step synthesis of a precursor in the existing pyrazolo [5, 1-a] isoindole compound synthesis process. According to the invention, a polarity reversal strategy is adopted, a cyano group is introduced into 1, 5-enyne to change the electronic characteristics of 1, 5-enyne, diazo, olefin and ethynyl benzene are reacted under mild conditions, two rings and three new chemical bonds are constructed through a series of intermolecular [3 + 2] cycloaddition, intramolecular cycloaddition and elimination reactions, and pyrazolo [5, 5-a]-1, 5-a-phenanthrene is efficiently synthesized. According to the present invention, the 1, 1-a] isoindole derivative has characteristics of good synthesis yield, simple operation of the synthesis method, easily available raw materials, good substrate universality and step economy, and provides the effective strategy for the drug design synthesis.
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