Work

Alkynyl Phenyl Selenides as Intermediates in the Metal‐Free Cyclisation of N‐Tosyl Homopropargyl Amides to γ‐Lactams

Year: 2024

Type: article

Abstract: In this work, we present an efficient Brønsted acid‐catalysed intramolecular hydroamination reaction of homopropargyl N‐tosyl amides to produce synthetically useful substituted γ‐lactams through the corresponding alkynyl phenyl selenide intermediates. Our focus on optimising the cyclisation protocol under flow conditions has led to a significant enhancement in efficiency, thereby reducing the time and resources required for the process. DFT calculations of the reaction mechanism for the catalytic transformation of a model alkynyl phenyl selenide were also conducted.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202401248

Authors: Andrea Temperini, Giulia Brufani, Stefano Santoro, Luigi Vaccaro

Institution: University of Perugia

Language: English

Topic: Organoselenium and organotellurium chemistry

Subfield: Toxicology

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

Funder: European Commission