3848-73-5Relevant academic research and scientific papers
Synthesis of Piperazines and Thiomorpholines by Ozonolysis of Cyclic Olefins and Reductive N-Alkylation
Kawaguchi, Mamoru,Hayashi, Osamu,Kanamoto, Masahiro,Hamada, Masayuki,Yamamoto, Yukio,Oda, Jun'ichi
, p. 435 - 440 (2007/10/02)
Ozonized 1-trifluoroacetyl-3-pyrroline (2a) and 3-sulfolene (6) were reduced with sodium cyanoborohydride (1) to afford the dialdehyde, which reacted in situ with the primary amines 3ad in the presence of 1 to give the piperazines 4ad (2160 percent) and the dioxothiomorpholines 7ad (2676 percent).Reduction of 7a and 7c with diisobutylaluminum hydride yielded the thiomorpholines 8a and 8c, respectively.On the other hand, the 9-membered azacrown ethers 10 and 11 were obtained when N,N'-dibenzylethylenediamine (9) was employed.The dioxothiomorpholine derivatives 13 of amino acids were also prepared by the same treatment.
