Poster (Scientific congresses and symposiums)
Unexpected formation of alkynyl-substituted 3-ylidenedihydrobenzo[ d]isothiazole 1,1-dioxides
Etse, Koffi Senam; Dassonneville, Benjamin; Zaragoza, Guillermo et al.
201620th Sigma-Aldrich Symposium
 

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Keywords :
benzoisothiazoles; Sonogashira coupling, X-ray; alkynyl ylidene dihydrobenzo[d]isothiazole dioxide
Abstract :
[en] The isothiazole chemistry has been some progress from the year 1956 and since then, their chemical and physical properties have been extensively studied. Due to their particular reactivity, isothiazoles have recently emerged as useful synthetic compounds and their applications in the search for alternative synthetic strategies and the development of novel molecular structures have been steadily growing [1]. The synthetic versatility of isothiazole has stemmed also from the interest in the biological and pharmacological properties of its derivatives [2]. A Pd-mediated one-step synthesis of benzoisothiazoles, involving the coupling of bromosulfoximine with terminal alkynes under Sonogashira coupling conditions, has parcially described [3]. Different ylidene dihydrobenzoisothiazole motif has been synthesised in one-pot conditions. Herein, we report palladium-copper metal catalyzed cyclization of 2-iodo-N-phenyl-N-((trimethylsilyl)ethynyl) benzensulfonamide in presence of terminal alkyne under Sonogashira coupling condition to afford substituted alkynyl ylidene dihydrobenzo[d]isothiazole dioxide. The resulting hydrobenzoisothiazole selectively gives the Z stereoisomer. X-ray molecular structures of compounds (Z)-3-(1,3-bis(trimethylsilyl) prop-2-yne-1-ylidene)-2-phenyl -2,3-dihydro benzo[d]isothiazole-1,1-dioxide, (Z)-3-(3-(3,5-dimethoxy phenyl)-1-(trmethylsilyl)prop-2-yne-1-phenyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide and (Z)-3-(3-(2-methoxy phenyl)-1-(trmethylsilyl)prop-2-yne-1-phenyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide are obtained. The mechanism f these reactions had been proposed.
Research center :
Chimie macromoléculaire et catalyse organique
Unidade de Difracción de Raios X (Universidade de Santiago de Compostela, Spain)
Disciplines :
Chemistry
Author, co-author :
Etse, Koffi Senam ;  Université de Liège - ULiège > Département de chimie > Chimie macromoléculaire et catalyse organique
Dassonneville, Benjamin;  Université de Liège - ULiège > Département de Chimie > Chimie macromoléculaire et catalyse organique
Zaragoza, Guillermo;  Universidade de Santiago de Compostela, Spain > Unidade de Difracción de Raios X, > Unidade de Difracción de Raios X,
Demonceau, Albert ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Language :
English
Title :
Unexpected formation of alkynyl-substituted 3-ylidenedihydrobenzo[ d]isothiazole 1,1-dioxides
Publication date :
08 December 2016
Number of pages :
A0
Event name :
20th Sigma-Aldrich Symposium
Event organizer :
Université libre de Bruxelles
Event place :
Blankenberge, Belgium
Event date :
du 08 au 09 décembre 2016
Available on ORBi :
since 17 January 2020

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