DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives

Rimpa De; Antony Savarimuthu; Tamal Ballav; Pijush Singh; Jayanta Nanda; Avantika Hasija; Deepak Chopra; Mrinal K. Bera

doi:10.1055/s-0040-1707909

DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives

Rimpa De, Antony Savarimuthu, Tamal Ballav, Pijush Singh, Jayanta Nanda, Avantika Hasija, Deepak Chopra, Mrinal K. Bera

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

10 Scopus citations

Abstract

A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.

Original language	English
Article number	st-2020-v0272-l
Pages (from-to)	1587-1592
Number of pages	6
Journal	Synlett
Volume	31
Issue number	16
DOIs	https://doi.org/10.1055/s-0040-1707909
State	Published - 1 Oct 2020
Externally published	Yes

Keywords

DBU
allenols
chalcones
organocatalysis
propargylic alcohols
rearrangement

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0040-1707909

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abstract = "A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.",

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T2 - An Efficient and Cost-Effective Route to Chalcone Derivatives

AU - De, Rimpa

AU - Savarimuthu, Antony

AU - Ballav, Tamal

AU - Singh, Pijush

AU - Nanda, Jayanta

AU - Hasija, Avantika

AU - Chopra, Deepak

AU - Bera, Mrinal K.

PY - 2020/10/1

Y1 - 2020/10/1

N2 - A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.

AB - A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.

KW - DBU

KW - allenols

KW - chalcones

KW - organocatalysis

KW - propargylic alcohols

KW - rearrangement

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U2 - 10.1055/s-0040-1707909

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DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives

Abstract

Keywords

ASJC Scopus subject areas

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