Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1 H-Isoindolin-1-Ones

Saira Mumtaz; Mark J Robertson; Michael Oelgemöller

doi:10.3390/molecules24244527

Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1 H-Isoindolin-1-Ones

Molecules. 2019 Dec 11;24(24):4527. doi: 10.3390/molecules24244527.

Authors

Saira Mumtaz¹, Mark J Robertson¹, Michael Oelgemöller^{1

2}

Affiliations

¹ College of Science and Engineering, James Cook University, Townsville, QLD 4811, Australia.
² Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4-bis, 9000 Gent, Belgium.

Abstract

An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical-thermal-thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times.

Keywords: arylmethylene isoindolinones; continuous-flow photochemistry; multi-step synthesis; photochemistry; photodecarboxylation; phthalimide.

MeSH terms

Decarboxylation
Isoindoles / chemical synthesis*
Isoindoles / chemistry
Molecular Structure
Photochemistry
Thermodynamics

Substances

Isoindoles

Grants and funding

DP130100794/Australian Research Council (ARC)