Data di Pubblicazione:
2018
Citazione:
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, M. Giustiniano. - In: GREEN CHEMISTRY. - ISSN 1463-9262. - 20:17(2018), pp. 3912-3915.
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.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
S. Pelliccia, V. Abbate, F. Meneghetti, N. Frascione, R.C. Hider, E. Novellino, G.C. Tron, M. Giustiniano
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