77910-25-9Relevant academic research and scientific papers
Reactivity of cyclic sulfamidates towards lithium acetylides: Synthesis of alkynylated amines
Eskici, Mustafa,Karanfil, Abdullah,?zer, M. Sabih,Sarikürkcü, Cengiz
, p. 6336 - 6341 (2011/12/22)
A synthetically useful level of reactivity of cyclic sulfamidates toward acetylides is described. Ring-opening reactions of a structurally diverse set of 1,2-and 1,3-cyclic sulfamidates with a range of lithium acetylides from aliphatic, cyclic, aromatic, heteroaromatic, and functionalized alkynes proceed smoothly in a regioselective manner to give the corresponding N-sulfate intermediates. Hydrolysis of these intermediates under acidic conditions furnishes the alkynylated amines in yields ranging from 29% to 98%. The scope of the acetylenic substitution reaction with the structural variations in both the cyclic sulfamidates and alkynes is briefly examined.
Synthesis of primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines
Gajda, Tadeusz,Napieraj, Anna,Osowska-Pacewicka, Krystyna,Zawadzki, Stefan,Zwierzak, Andrzej
, p. 4935 - 4946 (2007/10/03)
The novel ring-opening reaction of various 2-alkyl- and 2,2-dimethyl-N-(diethoxyphosphoryl)aziridines (1) and (10) with copper-modified Grignard reagents proceeds regiospecifically at the less hindered carbon. The diethyl N-sec-alkylphosphoramidates (2) thus obtained may efficiently be converted to primary sec-alkylamine hydrochlorides (3) by refluxing with 20% hydrochloric acid. 2,3-Disubstituted N-phosphorylated aziridines except N-phosphorylated cyclohexenimine (4) do not react under the described conditions. Copper-mediated reaction of 2-phenyl-N-(diethoxyphosphoryl)aziridine (7) with Grignard reagents affords a mixture of regioisomers (8) and (9) but still with the preference of ring-opening at the carbon of lesser substitution.
