235093-01-3Relevant academic research and scientific papers
The synthesis of novel oxa-azamacrocycles
Kuksa, Vladimir,Marshall, Colin,Wardell, Solange,Kong Thoo Lin, Paul
, p. 1034 - 1038 (2007/10/03)
Novel protected oxa-azamacrocycles 6a-f, 7a,c-f have been prepared by direct alkylation reaction between α,ω-bis[(2- mesitylsulfonyl)aminooxy]alkanes 2a-c and α,ω-bis(tosyl)alkanediols 3a,b in the presence of K2CO3 to give a mixture of the 1:1 (small macrocycles 6a- f) and 2:2 (large macrocycles 7a,c-f) adducts. Another method involved the reaction between bis (sulfonyl)amides 2a,b and ω-bromoalkanols 4a,b to give bis-alkanols 5a,b which were subsequently condensed with 2a,b under Mitsunobu conditions to give solely large macrocycles 7a,d in high yields. Macrocycle 7d was deprotected with HBr/HOAc to yield 8 as the tetrahydrobromide salt which was converted into its free base with methanolic KOH.
