(3+2) Annulation of Amidinothioureas with Binucleophile: Synthesis and Antimicrobial Activity of 3‐Phenylamino‐5‐aryl/alkyl‐1, 2, 4‐oxadiazole Derivatives. (12th May 2014)

• Record Type: Journal Article
• Authors: Yerande, Swapnil G.; Ghaisas, Amruta B.; Newase, Kiran M.; Wang, Wei; Wang, Kan; Dömling, Alexander
• Is Part Of: Journal of heterocyclic chemistry. Volume 51:Number 6(2014)
• Page Start: 1752
• Page End: 1756
• Publication Date: 2014-05-12
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.1873
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main" xml:lang="en" id="jhet1873-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p id="jhet1873-para-0002">Herein, we report an efficient method for preparation of 3‐phenylamino‐5‐aryl/alkyl‐1, 2, 4‐oxadiazole by (3+2) <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">annulation</named-content> 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 <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">antimicrobial activity</named-content> and showed promising inhibition of Gram‐positive bacteria (<italic>Staphylococcus aureus)</italic> and fungi (<italic>Candida albicans</italic>).</p> </abstract>