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

Research output: Contribution to journal › Article › 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.

Original language	English
Pages (from-to)	4419-4427
Number of pages	9
Journal	Synthesis
Volume	53
Issue number	23
DOIs	https://doi.org/10.1055/a-1543-3924
Publication status	Published - 13 Aug 2021
Externally published	Yes

Keywords

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

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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,

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

language = "English",

volume = "53",

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journal = "Synthesis",

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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

Y1 - 2021/8/13

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

UR - https://www.scopus.com/pages/publications/85113178547

U2 - 10.1055/a-1543-3924

DO - 10.1055/a-1543-3924

M3 - Article

SN - 0039-7881

VL - 53

SP - 4419

EP - 4427

JO - Synthesis

JF - Synthesis

IS - 23

ER -

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

Abstract

Keywords

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