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- Title
Synthesis of Mono-N-sulfonylimidazolidines by a 1,3-Dipolar Cycloaddition Strategy, as an Alternative to Selective NSulfonylation, and Their Ring Cleavage To Afford 1,2-Diamines.
- Authors
Laha, Joydev K.; Jethava, Krupal P.; Tummalapalli, K. S. Satyanarayana; Sharma, Sheetal
- Abstract
1,3-Dipolar cycloaddition between nonstabilized azomethine ylides and N-sulfonylimines has been developed, providing practical access to mono-N-sulfonylimidazolidines. The enhanced reactivity of N-sulfonylimines as dipolarophiles towards azomethine ylides largely eliminated possible Michael addition and favored 1,3-dipolar cycloaddition. Our approach could complement commonly practiced strategies for protection of imidazolidines. Furthermore, nucleophile-dependent ring cleavage of N-sulfonylimidazolidines produced synthetically useful mono-N-sulfonyl-1,2-diamines, which are otherwise difficult to obtain. Ring cleavage accompanied by CH2 extrusion, yielding mono-N-sulfonyl-1,2-diamines, occurred on treatment with TBAF, whereas N-methylated derivatives of N-sulfonyl-1,2-diamines were produced on treatment with LAH.
- Subjects
CHEMICAL synthesis; RING formation (Chemistry); SCHIFF bases; YLIDES; IMIDAZOLIDINES; NUCLEOPHILES
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 31, p4617
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201700654