Petasis Three-Component Coupling Reactions of Hydrazides for the Synthesis of Oxadiazolones and Oxazolidinones

Sebastian Thordal Le Quement; Thomas Flagstad; Remi Jacob Thomsen Mikkelsen; Mette Reimert Hansen; Michael C. Givskov; Thomas Eiland Nielsen

doi:10.1021/ol203280b

Petasis Three-Component Coupling Reactions of Hydrazides for the Synthesis of Oxadiazolones and Oxazolidinones

Sebastian Thordal Le Quement
, Thomas Flagstad
, Remi Jacob Thomsen Mikkelsen
, Mette Reimert Hansen
, Michael C. Givskov
, Thomas Eiland Nielsen

Department of Chemistry

University of Copenhagen

Research output: Contribution to journal › Journal article › Research › peer-review

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Abstract

An application of readily available hydrazides in the Petasis 3-component coupling reaction is presented. An investigation of the substrate scope was performed to establish a general, synthetically useful protocol for the formation of hydrazido alcohols, which were selectively converted to oxazolidinone and oxadiazolone ring systems through triphosgene-mediated cyclization reactions.

Original language	English
Journal	Organic Letters
Volume	14
Issue number	2
Pages (from-to)	640-643
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol203280b
Publication status	Published - 2012

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title = "Petasis Three-Component Coupling Reactions of Hydrazides for the Synthesis of Oxadiazolones and Oxazolidinones",

abstract = "An application of readily available hydrazides in the Petasis 3-component coupling reaction is presented. An investigation of the substrate scope was performed to establish a general, synthetically useful protocol for the formation of hydrazido alcohols, which were selectively converted to oxazolidinone and oxadiazolone ring systems through triphosgene-mediated cyclization reactions.",

author = "\{Le Quement\}, \{Sebastian Thordal\} and Thomas Flagstad and Mikkelsen, \{Remi Jacob Thomsen\} and Hansen, \{Mette Reimert\} and Givskov, \{Michael C.\} and Nielsen, \{Thomas Eiland\}",

year = "2012",

doi = "10.1021/ol203280b",

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volume = "14",

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journal = "Organic Letters",

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T1 - Petasis Three-Component Coupling Reactions of Hydrazides for the Synthesis of Oxadiazolones and Oxazolidinones

AU - Le Quement, Sebastian Thordal

AU - Flagstad, Thomas

AU - Mikkelsen, Remi Jacob Thomsen

AU - Hansen, Mette Reimert

AU - Givskov, Michael C.

AU - Nielsen, Thomas Eiland

PY - 2012

Y1 - 2012

N2 - An application of readily available hydrazides in the Petasis 3-component coupling reaction is presented. An investigation of the substrate scope was performed to establish a general, synthetically useful protocol for the formation of hydrazido alcohols, which were selectively converted to oxazolidinone and oxadiazolone ring systems through triphosgene-mediated cyclization reactions.

AB - An application of readily available hydrazides in the Petasis 3-component coupling reaction is presented. An investigation of the substrate scope was performed to establish a general, synthetically useful protocol for the formation of hydrazido alcohols, which were selectively converted to oxazolidinone and oxadiazolone ring systems through triphosgene-mediated cyclization reactions.

U2 - 10.1021/ol203280b

DO - 10.1021/ol203280b

M3 - Journal article

SN - 1523-7060

VL - 14

SP - 640

EP - 643

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Petasis Three-Component Coupling Reactions of Hydrazides for the Synthesis of Oxadiazolones and Oxazolidinones

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