142533-58-2Relevant academic research and scientific papers
Use of α-Bromo Oxime Ethers in the Synthesis of 1,2-Diamines
Shatzmiller, Shimon,Bercovici, Sorin
, p. 1005 - 1010 (2007/10/02)
Oxime ethers 1 react with ammonia and primary amines to give α-amino oxime ethers.The reaction of α-bromo oxime ethers with sodium azide affords α-azido oxime ethers.Hydrogenolysis of the azido compounds using 5percent palladium on calcium carbonate as catalyst yields the α-amino oxime ethers.The reaction of α-azido oxime ethers with lithium aluminum hydride gives 1,2-ethanediamine derivatives.The reaction of azido oxime ether 13 with LiAlH4, and subsequently the reaction of the resulting mixture of the diamines 14 and 15 with phosgene, preferably gives cis-4-pentyl-5-methyl-2-imidazolidone (16) indicating that the reduction of 13 proceeds in a stereoselective manner to furnish mainly the syn-1,2-ethanediamine 15. Key Words: Oxime ethers / α-Azido oxime ethers / α-Amino oxime ethers / 1,2-Ethanediamines
