28394-38-9Relevant academic research and scientific papers
Engaging Sulfonamides: Intramolecular Cross-Electrophile Coupling Reaction of Sulfonamides with Alkyl Chlorides
Castro, Anthony J.,Chen, Pan-Pan,Hewitt, Kirsten A.,Hong, Xin,Jarvo, Elizabeth R.,Lucas, Erika L.
, (2020/01/02)
The application of amine derivatives as coupling partners is rare due to the inherent strength of the C-N bond. Herein, we report the first cross-electrophile coupling reaction of unstrained benzylic sulfonamides. Nickel-catalyzed intramolecular cross-ele
Broadening the synthetic scope of the iron(III)-Catalyzed aza-prins cyclization
Carballo, Ruben M.,Valdomir, Guillermo,Purino, Martin,Martin, Victor S.,Padron, Juan I.
experimental part, p. 2304 - 2313 (2010/07/10)
The nature and influence of the N-sulfonyl group in azaPrins cyclization and the reactivity of the six-membered azacycle generated has been studied. The aza-Prins cyclization of γ,δ-unsaturated amines with a tosyl group at the nitrogen atom produces 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines with a halovlnyl function, extraordinarily stable to further derivatization and detosylation conditions. To modulate the reactivity of such aza-cycles, a general study of the azaPrins cyclization reaction was performed with several sulfonamides. Ring formation occurs satisfactorily with both N-nosyl and N-mesylamines providing optimal conditions for further synthetic transformations. To exemplify the scope of this methodology, a short synthesis of the alkaloid coniine was successfully carried out.
