On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

Sveva Pelliccia, Vincenzo Abbate, Fiorella Meneghetti, Nunzianda Frascione, Robert Charles Hider, Ettore Novellino, Gian Cesare Tron, Mariateresa Giustiniano

Research output: Contribution to journalArticlepeer-review

Abstract

The on-water reaction between 2-(sulfonylamino)-benzaldehydes, isocyanides and pyrrolidine is able to afford a library of poorly synthetically accessible 2-iminoisatins. The pyrrolidine exhibits for the first time the unique role of promoting a triple domino process, i.e.The formation of an N-Alkyl-2,3-diaminoindole, the sulfonamide heterolytic N-S bond cleavage, and the hydrolysis of the resulting iminium ion, with the loss of p-Toluenesulfinic acid. RP HPLC-DAD and UHPLC-HRMS real-Time monitoring of the reaction provided experimental data that support the reaction mechanism. The use of water as a solvent under ultrasound catalysis and the convergent nature of this approach allow, for the first time, a green and sustainable synthesis of 2-iminoisatins.

Original languageEnglish
Pages (from-to)3912-3915
Number of pages4
JournalGreen Chemistry
Volume20
Issue number17
DOIs
Publication statusPublished - 2018

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