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

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer 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.

Lingua originale	Inglese
pagine (da-a)	3912-3915
Numero di pagine	4
Rivista	Green Chemistry
Volume	20
Numero di pubblicazione	17
DOI	https://doi.org/10.1039/c8gc01090k
Stato di pubblicazione	Pubblicato - 2018

Accesso al documento

10.1039/c8gc01090k

Altri file e collegamenti

Link to publication in Scopus

Cita questo

@article{dfb237dc4f1c43cdbf70ce097c45f8f3,

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 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.",

author = "Sveva Pelliccia and Vincenzo Abbate and Fiorella Meneghetti and Nunzianda Frascione and Hider, {Robert Charles} and Ettore Novellino and Tron, {Gian Cesare} and Mariateresa Giustiniano",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8gc01090k",

language = "English",

volume = "20",

pages = "3912--3915",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "Royal Society of Chemistry",

number = "17",

}

TY - JOUR

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

Y1 - 2018

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 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.

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 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.

UR - http://www.scopus.com/inward/record.url?scp=85052682325&partnerID=8YFLogxK

U2 - 10.1039/c8gc01090k

DO - 10.1039/c8gc01090k

M3 - Article

SN - 1463-9262

VL - 20

SP - 3912

EP - 3915

JO - Green Chemistry

JF - Green Chemistry

IS - 17

ER -

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

Abstract

Accesso al documento

Altri file e collegamenti

Fingerprint

Cita questo