Petasis three-component coupling reactions of hydrazides for the synthesis of oxadiazolones and oxazolidinones

Sebastian T Le Quement; Thomas Flagstad; Remi J T Mikkelsen; Mette R Hansen; Michael Givskov; Thomas E Nielsen

doi:10.1021/ol203280b

Petasis three-component coupling reactions of hydrazides for the synthesis of oxadiazolones and oxazolidinones

Sebastian T Le Quement, Thomas Flagstad, Remi J T Mikkelsen, Mette R Hansen, Michael Givskov, Thomas E Nielsen

Department of Immunology and Microbiology

24 Citations (Scopus)

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
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol203280b
Publication status	Published - 20 Jan 2012

Keywords

Aldehydes
Cyclization
Hydrazines
Molecular Structure
Oxazolidinones

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10.1021/ol203280b

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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.",

keywords = "Aldehydes, Cyclization, Hydrazines, Molecular Structure, Oxazolidinones",

author = "{Le Quement}, {Sebastian T} and Thomas Flagstad and Mikkelsen, {Remi J T} and Hansen, {Mette R} and Michael Givskov and Nielsen, {Thomas E}",

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T1 - Petasis three-component coupling reactions of hydrazides for the synthesis of oxadiazolones and oxazolidinones

AU - Le Quement, Sebastian T

AU - Flagstad, Thomas

AU - Mikkelsen, Remi J T

AU - Hansen, Mette R

AU - Givskov, Michael

AU - Nielsen, Thomas E

PY - 2012/1/20

Y1 - 2012/1/20

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.

KW - Aldehydes

KW - Cyclization

KW - Hydrazines

KW - Molecular Structure

KW - Oxazolidinones

U2 - 10.1021/ol203280b

DO - 10.1021/ol203280b

M3 - Journal article

C2 - 22233295

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

Abstract

Keywords

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