Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives

Camilla Russo; Rolando Cannalire; Paolo Luciano; Francesca Brunelli; Gian Cesare Tron; Mariateresa Giustiniano

doi:10.1055/a-1543-3924

Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives

Camilla Russo, Rolando Cannalire, Paolo Luciano, Francesca Brunelli, Gian Cesare Tron, Mariateresa Giustiniano

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

Abstract

A new visible-light photocatalytic multicomponent reaction (MCR) involving N-alkyl-N-methylanilines, N-isocyanoiminotriphenylphosphorane, and carboxylic acids leading to 1,3,4-oxadiazole derivatives is reported. The developed mild reaction conditions enable a broad substrate scope and good functional group tolerance, as further highlighted in the late-stage functionalization of amino acids and drugs. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines is also reported.

Lingua originale	Inglese
pagine (da-a)	4419-4427
Numero di pagine	9
Rivista	Synthesis
Volume	53
Numero di pubblicazione	23
DOI	https://doi.org/10.1055/a-1543-3924
Stato di pubblicazione	Pubblicato - 13 ago 2021
Pubblicato esternamente	Sì

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10.1055/a-1543-3924

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title = "Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives",

abstract = "A new visible-light photocatalytic multicomponent reaction (MCR) involving N-alkyl-N-methylanilines, N-isocyanoiminotriphenylphosphorane, and carboxylic acids leading to 1,3,4-oxadiazole derivatives is reported. The developed mild reaction conditions enable a broad substrate scope and good functional group tolerance, as further highlighted in the late-stage functionalization of amino acids and drugs. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines is also reported.",

keywords = "1,3,4-oxadiazoles, Ugi reaction, aza-Wittig reaction, isocyanide chemistry, multicomponent reactions, photoredox catalysis",

author = "Camilla Russo and Rolando Cannalire and Paolo Luciano and Francesca Brunelli and Tron, {Gian Cesare} and Mariateresa Giustiniano",

year = "2021",

month = aug,

day = "13",

doi = "10.1055/a-1543-3924",

language = "English",

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T1 - Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives

AU - Russo, Camilla

AU - Cannalire, Rolando

AU - Luciano, Paolo

AU - Brunelli, Francesca

AU - Tron, Gian Cesare

AU - Giustiniano, Mariateresa

PY - 2021/8/13

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N2 - A new visible-light photocatalytic multicomponent reaction (MCR) involving N-alkyl-N-methylanilines, N-isocyanoiminotriphenylphosphorane, and carboxylic acids leading to 1,3,4-oxadiazole derivatives is reported. The developed mild reaction conditions enable a broad substrate scope and good functional group tolerance, as further highlighted in the late-stage functionalization of amino acids and drugs. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines is also reported.

AB - A new visible-light photocatalytic multicomponent reaction (MCR) involving N-alkyl-N-methylanilines, N-isocyanoiminotriphenylphosphorane, and carboxylic acids leading to 1,3,4-oxadiazole derivatives is reported. The developed mild reaction conditions enable a broad substrate scope and good functional group tolerance, as further highlighted in the late-stage functionalization of amino acids and drugs. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines is also reported.

KW - 1,3,4-oxadiazoles

KW - Ugi reaction

KW - aza-Wittig reaction

KW - isocyanide chemistry

KW - multicomponent reactions

KW - photoredox catalysis

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DO - 10.1055/a-1543-3924

M3 - Article

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JO - Synthesis

JF - Synthesis

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ER -

Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives

Abstract

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