51243-13-1Relevant academic research and scientific papers
(3+2) annulation of amidinothioureas with binucleophile: Synthesis and antimicrobial activity of 3-phenylamino-5-aryl/alkyl-1,2, 4-oxadiazole derivatives
Yerande, Swapnil G.,Ghaisas, Amruta B.,Newase, Kiran M.,Wang, Wei,Wang, Kan,D?mling, Alexander
, p. 1752 - 1756 (2015/01/09)
Herein, we report an efficient method for preparation of 3-phenylamino-5-aryl/alkyl-1,2,4-oxadiazole by (3+2) annulation of amidinothioureas with binucleophilic hydroxylamine hydrochloride in the presence of mercury (II) chloride. Desired 3-phenylamino-5-aryl/alkyl-1,2,4-oxadiazole was prepared in good to moderate yields. On the basis of the literature precedence, the mechanism for the formation of 3-phenylamino- 5-aryl/alkyl-1,2,4-oxadiazole is proposed. The synthesized compounds were tested for their antimicrobial activity and showed promising inhibition of Gram-positive bacteria (Staphylococcus aureus) and fungi (Candida albicans).
A diversified assembly of 1,2,4-oxadiazol-3-amines: Metallic thiophile catalyzed chemoselective one-pot reaction of aryl isothiocyanates, amidines/guanidines, and hydroxylamine
Jalani, Hitesh B.,Sudarsanam, V.,Vasu, Kamala K.
, p. 3378 - 3386,9 (2012/12/12)
An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exo-trig cyclization.
