5-Annulation of Ketoimines: TFA-Catalyzed Construction of Isoindolinone-3-carboxylates and Development of Photophysical Properties
- Anirban KayetAnirban KayetDepartment of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata 700009, IndiaMore by Anirban Kayet
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- Sk AjarulSk AjarulDepartment of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata 700009, IndiaMore by Sk Ajarul
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- Sima PaulSima PaulDepartment of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata 700009, IndiaMore by Sima Paul
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- Dilip K. Maiti*Dilip K. Maiti*E-mail: [email protected]Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata 700009, IndiaMore by Dilip K. Maiti
Abstract
Herein we have demonstrated the first report on 5-annulation of ketoimines to valuable isoindolinone-3-carboxylates. Instead of commonly used aldimine substrates, relatively less reactive ketoimines are employed for developing a TFA catalyzed organoreductive cyclization to furnish a variety of isoindolinones in excellent yield and reaction rate under mild reaction conditions. This is a metal-free event, which proceeds through a one pot ketoimine formation, hydride transfer from an organic reductant 2-(naphthalen-2-yl)-2,3-dihydrobenzo[d]thiazole, and followed by five member cyclization sequences through TFA-activation of imine and ester groups. Studies on ESI-MS kinetics, leaving group aptitude, and control experiments led us to propose the mechanistic pathway of the new ketoimine-lactamization reaction. We have shown the synthetic utility of the emerging synthons through easy transformation of isoindolinones to different synthetic analogues. We investigated photophysical properties of the small molecules for their futuristic application as a pharmaceutical and materials, and the heterocycles displayed brilliant fluorescence activity.
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