a new class of heterocycles 1,4,3,5-oxathiadiazepane 4,4-dioxides一个新类杂环化合物1的4 3 4-dioxides 5-oxathiadiazepane 4日.pdfVIP

Molecules 2012, 17, 1890-1899; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article A New Class of Heterocycles: 1,4,3,5-Oxathiadiazepane 4,4-dioxides Amel Bendjeddou 1,*, Tahar Abbaz 2, Zine Regainia 1 and Nour-Eddine Aouf 1 1 Laboratoire de Chimie Organique Appliquée, Groupe de chimie Hétérocyclique, Département de Chimie, Faculté des Sciences, Université d’Annaba, BP 12, 23000, Algérie 2 Laboratoire de Chimie des Matériaux Organiques, Université de Tébessa, Route de Constantine, Tébessa, 12000, Algérie * Author to whom correspondence should be addressed; E-Mail: bendjeddouamel@; Fax: +213-3095-2935. Received: 19 January 2012; in revised form: 6 February 2012 / Accepted: 8 February 2012 / Published: 14 February 2012 Abstract: This work reports the synthesis of novel 1,4,3,5-oxathiadiazepanes 4,4-dioxides from the reaction of N ’-benzyl-N-(2-hydroxyethyl)-sarcosine or proline sulfamide with aromatic aldehydes under acid catalysis. To prepare the starting materials N-Boc-sulfamide derivatives of sarcosine or proline were alkylated with benzyl alcohol under Mitsunobu reaction conditions, the Boc group was removed chemoselectively by acidolysis, and the resulting product reduced to the corresponding alcohol in good yields. Keywords: cyclic sulfamides; benzodithiazine dioxides; benzoxathiazepine dioxides 1. Introduction Sulfamides and their analogs have a rich chemical and biological history and have emerged as a promising class of compounds in drug discov