A New Sustainable Synthesis of N-aryl Oxazolidin-2-ones by the Cycloaddition Reaction of CO

A New Sustainable Synthesis of N-aryl Oxazolidin-2-ones by the Cycloaddition Reaction of CO ₂ to

N-aryl Aziridines

A New Sustainable Synthesis of N-aryl Oxazolidin-2-ones by the Cycloaddition Reaction of CO ₂ to

N-aryl Aziridines

Paolo Sonzini, Università degli studi di Milano paolo.sonzini@unimi.it

IC-CCU, Bari, 5

and 6

of December 2019 Paolo Sonzini, Università degli studi di Milano paolo.sonzini@unimi.it

IC-CCU, Bari, 5

and 6

of December 2019

The CO ₂

cycloadditio n reaction

The CO ₂

cycloadditio n reaction

2

Optimizatio n and Scope Optimizatio n and Scope

Why

Oxazalidinon es

Why

Oxazalidinon

Optimization es

and scope

Optimization and scope

3

Optimized pressure: 1.2 MPa Optimized temperature: 125 °C Optimized concentration: 1.5 M Optimized reaction time: 8 h

Optimized cat/co-cat/substrate ratio: 1:5:100

Synthesis of 19 differently substituted N-aryl

Oxazolidinones

Why

Oxazalidinon es

Why

Oxazalidinon es

Oxazolidinone s as emerging drugs

Oxazolidinone s as emerging drugs

4

J. Fujimoto et al; Journal of Medicinal Chemistry 2017 60 (21), 8963-8981 Glenn W Kaatz & Michael J Rybak, Emerging Drugs, 2001 6 (1), 43-55 W. Mhay, P. Plucinski, C. Frost, Organic Letters, 2014 16 (19), 5020-5023

Tandem reaction Tandem reaction

From Azides to Oxazolidinones:

a two step-one pot

methodology

From Azides to Oxazolidinones:

a two step-one pot

methodology

5

• High atom economy;

• The only by-product is N

;

• The catalysts are not toxic;

• The first catalyst does not affect the yield of the second step;

• Just two synthetic steps;

• Cheap raw materials and

catalysts.

Paolo Sonzini, Università degli studi di Milano paolo.sonzini@unimi.it

Paolo Sonzini, Università degli studi di Milano

paolo.sonzini@unimi.it