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Updated: May 31, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

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Published on: February 15, 2016

Mechanochemical Single-Carbon Insertion into (Iso)quinolines.

Chunxiu Jing¹, Fanchen Huang¹, Xiaotong Liang¹

¹Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710069, China.

Nature Communications

|May 29, 2026

Summary

Researchers developed a new mechanochemical method to convert (iso)quinolines into benzoazepines. This efficient skeletal editing technique offers a valuable route to diverse benzoazepine drug candidates under mild conditions.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Published on: June 20, 2014

Area of Science:

Organic Chemistry
Medicinal Chemistry
Synthetic Chemistry

Background:

(Iso)quinolines are prevalent scaffolds in FDA-approved drugs.
Benzoazepines are underrepresented in drug discovery due to limited synthetic accessibility.
Efficient methods for benzoazepine synthesis are highly desirable.

Purpose of the Study:

To develop an efficient protocol for converting (iso)quinolines into benzoazepines.
To explore the utility of mechanochemical skeletal editing for carbon-atom insertion.
To demonstrate the application of this method to pharmaceutically relevant compounds.

Main Methods:

Mechanochemical skeletal editing via carbon-atom insertion into (iso)quinolines.
Ambient reaction conditions, avoiding metal additives, bulk solvent, and pre-activation.
Investigation of substrate scope and reaction mechanism.
Photochemical cycloaddition of benzoazepines and subsequent de-carbonylation.

Main Results:

Successful conversion of (iso)quinolines to benzoazepines using a user-friendly mechanochemical protocol.
The reaction proceeds efficiently under mild, solvent-free conditions.
Demonstrated light-induced cycloaddition of benzoazepines to cyclobutene-fused indolines.
Conversion of indolines to indoles via selective de-carbonylation.

Conclusions:

A novel and efficient mechanochemical method for synthesizing benzoazepines from (iso)quinolines has been established.
This skeletal editing approach provides access to diverse benzoazepine structures.
The protocol's utility is validated through its application to pharmaceutically relevant (iso)quinolines and further transformations.