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

Saira Mumtaz,Mark J Robertson,Michael Oelgemöller

doi:10.3390/molecules24244527

Saira Mumtaz, Mark J Robertson + Show 1 more

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https://doi.org/10.3390/molecules24244527

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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.

Highlights

Z-selectivity as determined by conditions of the subsequent dehydration step led to the formation of its corresponding aldol condensation product, which demanded additional time- and resource-intensive separation
General experimental details and spectroscopic data can be found in the supporting information
The spectroscopic data are in full agreement with those reported in the literature [6]

Summary

Introduction

Due to broad their biological broadactivities, biological activities, the synthesis of Due to their the synthesis of 3-arylmethylene-2,3-dihydro-1H3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones has been widely studied [1,2]. Among the many synthetic pathways developed, the many synthetic pathways developed, the photodecarboxylative phthalimides photodecarboxylative benzylation of phthalimides represents a mildbenzylation and efficientofaccess to these represents a mild and efficient access to these important target compounds [3,4]. This important target compounds [3,4].

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