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Issue 17, 2018
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On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

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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.

Graphical abstract: On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

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Publication details

The article was received on 06 Apr 2018, accepted on 19 Jul 2018 and first published on 25 Jul 2018


Article type: Communication
DOI: 10.1039/C8GC01090K
Citation: Green Chem., 2018,20, 3912-3915
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    On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

    S. Pelliccia, V. Abbate, F. Meneghetti, N. Frascione, R. C. Hider, E. Novellino, G. C. Tron and M. Giustiniano, Green Chem., 2018, 20, 3912
    DOI: 10.1039/C8GC01090K

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