Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

Cristiana Necardo; Antonella Ilenia Alfano; Erika Del Grosso; Sveva Pelliccia; Ubaldina Galli; Ettore Novellino; Fiorella Meneghetti; Mariateresa Giustiniano; Gian Cesare Tron

doi:10.1021/acs.joc.9b02546

Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

Cristiana Necardo
, Antonella Ilenia Alfano
, Erika Del Grosso
, Sveva Pelliccia
, Ubaldina Galli
, Ettore Novellino
, Fiorella Meneghetti
, Mariateresa Giustiniano
, Gian Cesare Tron

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C-H into the final product.

Original language	English
Pages (from-to)	16299-16307
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	84
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.9b02546
Publication status	Published - 20 Dec 2019

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title = "Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles",

abstract = "Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C-H into the final product.",

author = "Cristiana Necardo and Alfano, \{Antonella Ilenia\} and \{Del Grosso\}, Erika and Sveva Pelliccia and Ubaldina Galli and Ettore Novellino and Fiorella Meneghetti and Mariateresa Giustiniano and Tron, \{Gian Cesare\}",

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year = "2019",

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doi = "10.1021/acs.joc.9b02546",

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T1 - Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction

T2 - A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

AU - Necardo, Cristiana

AU - Alfano, Antonella Ilenia

AU - Del Grosso, Erika

AU - Pelliccia, Sveva

AU - Galli, Ubaldina

AU - Novellino, Ettore

AU - Meneghetti, Fiorella

AU - Giustiniano, Mariateresa

AU - Tron, Gian Cesare

PY - 2019/12/20

Y1 - 2019/12/20

N2 - Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C-H into the final product.

AB - Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C-H into the final product.

UR - https://www.scopus.com/pages/publications/85076817516

U2 - 10.1021/acs.joc.9b02546

DO - 10.1021/acs.joc.9b02546

M3 - Article

SN - 0022-3263

VL - 84

SP - 16299

EP - 16307

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

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