181513-69-9Relevant academic research and scientific papers
An Efficient Synthetic Method of 4-Penteneselenoamides: Four-Component Coupling Reaction of Terminal Acetylenes, Selenium, Amines, and Allylic Bromides
Murai, Toshiaki,Ezaka, Tatsuya,Kato, Shinzi
, p. 1193 - 1200 (1998)
The reaction of lithium alkyneselenolates generated from terminal acetylenes, butyllithium, and selenium with amines and allylic bromides proceeded smoothly in THF at 67°C to give 4-penteneselenoamides in moderate to high yields. The reaction may proceed via selenoketene intermediates bearing an allylic group, followed by the attack of amines to give the products. Aliphatic and aromatic acetylenes, silylacetylene, and enynes were employed as terminal acetylenes. One molar amount of secondary amines was effective, whereas an excess of primary amines was necessary. The reactions with 2-hulenyl bromide exhibited high regioselectivity, although they gave the stereoisomeric mixtures. The reactions of silyl ethers of propargylic alcohols gave α,β-unsaturated selenoamides as a product.
Highly efficient one-pot synthesis of α,α-disubstituted selenoamides and their first reduction to amines
Murai, Toshiaki,Ezaka, Tatsuya,Kanda, Takahiro,Kato, Shinzi
, p. 1809 - 1810 (2007/10/03)
α,α-Disubstituted selenoamides are synthesized from terminal acetylenes, selenium, amines and allylic bromides in good to high yields; their reduction with LiAlH4 affords alkenylamines quantitatively.
