Abstract

A library of N 1-arylated 5-phenyl-1,3-dihydro-2 H -1,4-benzodiazepin-2-ones has been synthesized starting with unsymmetrical diaryliodonium salts using aqueous ammonia as a base. This can also be applied to a similar 1,3,4-benzotriazepin-2-one derivative.

Highlights

  • Being able to generate libraries of diverse analogues, in this case by adding N-functionality to a privileged core unit, using mild and efficient methodologies, can substantially improve SAR studies and optimise the drug development process potentially repurposing privileged scaffolds for new biological targets

  • In transition-metal-free processes unsymmetrical diaryliodonium salts give a mixture of products where both groups are transferred and the transfer of more sterically hindered and electron-with

  • The ether product is only observed in substantial amounts when the benzodiazepine substrates react poorly with the diaryliodonium salts (Table 4)

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Summary

Introduction

Being able to generate libraries of diverse analogues, in this case by adding N-functionality to a privileged core unit, using mild and efficient methodologies, can substantially improve SAR studies (structure–activity relationship) and optimise the drug development process potentially repurposing privileged scaffolds for new biological targets.24,25. Novak et al recently reported a protocol for the N-arylation of pyrazoles.36 A quick screen of conditions, adapting this protocol using diaryliodonium salts with weak bases under mild conditions, showed that it was possible to perform similar arylations on the 1,4-benzodiazepine system. Upon initial screening of a number of solvents, 1,2dichloroethane (DCE) was found to give the best results (Table 1, entry 2). A series of functionalized 1,4-benzodiazepines was N-arylated using (4-nitrophenyl)phenyliodonium triflate in good to excellent yields (Scheme 1).

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