Dibenzo[b,e]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intra­molecular Heck Reaction and Application towards Drug-Like Small Molecules

Arijit Das; Arup Maiti; Mrinalkanti Kundu; Kuldeep K. Roy; Inul Ansary

doi:10.1055/s-0037-1611548

Synthesis, Table of Contents

Synthesis 2019; 51(17): 3231-3240
DOI: 10.1055/s-0037-1611548

paper

Dibenzo[b,e]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intramolecular Heck Reaction and Application towards Drug-Like Small Molecules

Arijit Das

^aDepartment of Chemistry, The University of Burdwan, Burdwan-713104, West Bengal, India Email: iansary@chem.buruniv.ac.in

,

Arup Maiti

^bTCG Lifesciences Pvt. Ltd., BN-7, Salt Lake, Kolkata-700091, West Bengal, India Email: mrinal.kundu@tcgls.com

,

Mrinalkanti Kundu*

^bTCG Lifesciences Pvt. Ltd., BN-7, Salt Lake, Kolkata-700091, West Bengal, India Email: mrinal.kundu@tcgls.com

,

Kuldeep K. Roy

^cNational Institute of Pharmaceutical Education and Research, 168 Maniktala Main Road, Kolkata- 700054, West Bengal, India

,

Inul Ansary*

^aDepartment of Chemistry, The University of Burdwan, Burdwan-713104, West Bengal, India Email: iansary@chem.buruniv.ac.in

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Abstract

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Abstract

A new, convenient synthesis of dibenzo[b,e]azepin-6-ones and seven-membered sultam derivatives have been envisaged via Pd-catalyzed regioselective intramolecular Heck reaction of the corresponding easily accessible precursors. This protocol has been successfully implemented to synthesize N-methyldarenzepine in four steps and in good yield. Moreover, one of the intermediates has been utilized for the synthesis of a new analogue of darenzepine. Preliminary modeling studies were performed to investigate the binding potential to muscarinic acetylcholine receptor (M4).

Key words

intramolecular Heck reaction - regioselectivity - dibenzo[b,e]azepin-6-ones - seven-membered sultams - docking - M4 receptor

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References

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Supplementary Material

Supporting Information

Dibenzo[b,e]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intra­molecular Heck Reaction and Application towards Drug-Like Small Molecules

Dibenzo[b,e]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intramolecular Heck Reaction and Application towards Drug-Like Small Molecules