Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

Abstract

A one-pot three-component synthesis of substituted meta-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of meta-hetarylanilines prepared (21–85% isolated yield) demonstrates the synthetic utility of the developed method.

Keywords

• aniline
• benzannulation
• condensation
• 1,3-diketone
• hammett constants
• terphenyl