the reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with sulfimides a new synthesis of n-aryl-1,2,3-dithiazolimines4,的反应5-dichloro-1 2 3-dithiazolium氯n-aryl-1 sulfimides新合成的2,3-dithiazolimines.pdfVIP

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the reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with sulfimides a new synthesis of n-aryl-1,2,3-dithiazolimines4,的反应5-dichloro-1 2 3-dithiazolium氯n-aryl-1 sulfimides新合成的2,3-dithiazolimines.pdf

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the reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with sulfimides a new synthesis of n-aryl-1,2,3-dithiazolimines4,的反应5-dichloro-1 2 3-dithiazolium氯n-aryl-1 sulfimides新合成的2,3-dithiazolimines

Molecules 2009, 14, 2356-2362; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article The Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with Sulfimides: A New Synthesis of N-Aryl-1,2,3-dithiazolimines Andreas S. Kalogirou and Panayiotis A. Koutentis * Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus; E-mail: andreas_ch05@ (A-S.K.) * Author to whom correspondence should be addressed; E-mail: koutenti@ucy.ac.cy; Tel.: +35722892783; Fax: +35722892809 Received: 26 May 2009; in revised form: 10 June 2009 / Accepted: 12 June 2009 / Published: 2 July 2009 Abstract: N-Aryl-S,S-dimethylsulfimides 3 (Ar = 4-NO C H ), 4 (Ar = Ph) and 5 (Ar = 4- 2 6 4 Tol) react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3- dithiazolylidene)benzenamines 8 (Ar = 4-NO C H ), 9 (Ar = Ph) and 10 (Ar = 4-Tol) in 2 6 4 84, 94 and 87% yields, respectively. The reaction proceeds in the absence of base and a proposed reaction mechanism is given. Keywords: dithiazole; dithiazolimine; sulfimide; sulfilimine; heteroarene; appel salt 1. Introduction N-Aryl-1,2,3-dithiazol-5H-imines show interesting antitumour [1], antibacterial [2-4], antifungal [5- 7], and herbicidal [8] activities. The biological activity could be due to the 1,2,3-dithiazole ring, which acts as a powerful inhibitor of several enzymes that are