Efficient preparations of novel ynamides and allenamides

Lin Li Wei; Jason A. Mulder; Hui Xiong; Craig A. Zificsak; Christopher J. Douglas; Richard P. Hsung

doi:10.1016/S0040-4020(00)01014-0

Efficient preparations of novel ynamides and allenamides

Lin Li Wei, Jason A. Mulder, Hui Xiong, Craig A. Zificsak, Christopher J. Douglas, Richard P. Hsung

Chemistry (Twin Cities)

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

135 Scopus citations

Abstract

Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.

Original language	English (US)
Pages (from-to)	459-466
Number of pages	8
Journal	Tetrahedron
Volume	57
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4020(00)01014-0
State	Published - Jan 14 2001

Bibliographical note

Funding Information:
R. P. H. thanks the American Cancer Society for an institutional grant [IRG-58-001-40-IRG-26]. R. P. H. also thanks R. W. Johnson Pharmaceutical Institute for a generous grant from the Focused Giving Program. C. J. D. thanks Pharmacia-Upjohn and UMN Department of Chemistry Lando/NSF Program for Summer Research Fellowships.

Keywords

Allenamides
Bromination
Ynamides

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title = "Efficient preparations of novel ynamides and allenamides",

abstract = "Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.",

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note = "Funding Information: R. P. H. thanks the American Cancer Society for an institutional grant [IRG-58-001-40-IRG-26]. R. P. H. also thanks R. W. Johnson Pharmaceutical Institute for a generous grant from the Focused Giving Program. C. J. D. thanks Pharmacia-Upjohn and UMN Department of Chemistry Lando/NSF Program for Summer Research Fellowships. ",

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AU - Wei, Lin Li

AU - Mulder, Jason A.

AU - Xiong, Hui

AU - Zificsak, Craig A.

AU - Douglas, Christopher J.

AU - Hsung, Richard P.

N1 - Funding Information: R. P. H. thanks the American Cancer Society for an institutional grant [IRG-58-001-40-IRG-26]. R. P. H. also thanks R. W. Johnson Pharmaceutical Institute for a generous grant from the Focused Giving Program. C. J. D. thanks Pharmacia-Upjohn and UMN Department of Chemistry Lando/NSF Program for Summer Research Fellowships.

PY - 2001/1/14

Y1 - 2001/1/14

N2 - Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.

AB - Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.

KW - Allenamides

KW - Bromination

KW - Ynamides

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SP - 459

EP - 466

JO - Tetrahedron

JF - Tetrahedron

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ER -

Efficient preparations of novel ynamides and allenamides

Abstract

Bibliographical note

Keywords

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