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

doi:10.1039/C8GC01090K

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

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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 a N-alkyl-2,3-diaminoindole, the sulfonamide heterolytic N-S bond cleavage, and the hydrolysis of the resulting imminium ion, with loss of p-toluensulfinic acid. RP HPLC-DAD and UHPLC-HRMS real-time monitoring of the reaction provided experimental data that supports the reaction mechanism. The use of water as 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 language	English
Journal	GREEN CHEMISTRY
Early online date	25 Jul 2018
DOIs	https://doi.org/10.1039/C8GC01090K
Publication status	E-pub ahead of print - 25 Jul 2018

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On-water pyrrolidine-mediated_PELLICCIA_Firstonline25July2018_GREEN AAMAccepted author manuscript, 558 KB

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title = "On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins",

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 a N-alkyl-2,3-diaminoindole, the sulfonamide heterolytic N-S bond cleavage, and the hydrolysis of the resulting imminium ion, with loss of p-toluensulfinic acid. RP HPLC-DAD and UHPLC-HRMS real-time monitoring of the reaction provided experimental data that supports the reaction mechanism. The use of water as solvent under ultrasound catalysis, and the convergent nature of this approach, allow for the first time a green and sustainable synthesis of 2-iminoisatins.",

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year = "2018",

month = jul,

day = "25",

doi = "10.1039/C8GC01090K",

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T1 - On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

AU - Pelliccia, Sveva

AU - Abbate, Vincenzo

AU - Meneghetti, Fiorella

AU - Frascione, Nunzianda

AU - Hider, Robert Charles

AU - Novellino, Ettore

AU - Tron, Gian Cesare

AU - Giustiniano, Mariateresa

PY - 2018/7/25

Y1 - 2018/7/25

N2 - 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 a N-alkyl-2,3-diaminoindole, the sulfonamide heterolytic N-S bond cleavage, and the hydrolysis of the resulting imminium ion, with loss of p-toluensulfinic acid. RP HPLC-DAD and UHPLC-HRMS real-time monitoring of the reaction provided experimental data that supports the reaction mechanism. The use of water as solvent under ultrasound catalysis, and the convergent nature of this approach, allow for the first time a green and sustainable synthesis of 2-iminoisatins.

AB - 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 a N-alkyl-2,3-diaminoindole, the sulfonamide heterolytic N-S bond cleavage, and the hydrolysis of the resulting imminium ion, with loss of p-toluensulfinic acid. RP HPLC-DAD and UHPLC-HRMS real-time monitoring of the reaction provided experimental data that supports the reaction mechanism. The use of water as solvent under ultrasound catalysis, and the convergent nature of this approach, allow for the first time a green and sustainable synthesis of 2-iminoisatins.

U2 - 10.1039/C8GC01090K

DO - 10.1039/C8GC01090K

M3 - Article

SN - 1463-9262

JO - GREEN CHEMISTRY

JF - GREEN CHEMISTRY

ER -

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

Abstract

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