Efficient preparations of novel ynamides and allenamides

LL Wei, JA Mulder, H Xiong, CA Zificsak, CJ Douglas…

Index: Wei, Lin-Li; Mulder, Jason A.; Xiong, Hui; Zificsak, Craig A.; Douglas, Christopher J.; Hsung, Richard P. Tetrahedron, 2001 , vol. 57, # 3 p. 459 - 466

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Citation Number: 115

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 ...