Synthesis 2016; 48(09): 1344-1352
DOI: 10.1055/s-0035-1561371
paper
© Georg Thieme Verlag Stuttgart · New York

Solvent-Free Condensation Reactions To Synthesize Five-Membered Heterocycles Containing the Sulfamide Fragment

Nelson Rodríguez Arroyo
a  Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA, CCT La Plata-CONICET), Facultad de Ciencias Exactas, Departamento de Química, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal 4, 1900 La Plata, Argentina
,
María F. Rozas
a  Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA, CCT La Plata-CONICET), Facultad de Ciencias Exactas, Departamento de Química, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal 4, 1900 La Plata, Argentina
,
Patricia Vázquez
b  Centro de Investigación y Desarrollo en Ciencias Aplicadas ‘Dr. J. J. Ronco’ (CINDECA), Departamento de Química, Facultad de Ciencias Exactas, UNLP-CCT-CONICET, Calle 47 No 257, 1900 La Plata, Argentina
,
Gustavo P. Romanelli
b  Centro de Investigación y Desarrollo en Ciencias Aplicadas ‘Dr. J. J. Ronco’ (CINDECA), Departamento de Química, Facultad de Ciencias Exactas, UNLP-CCT-CONICET, Calle 47 No 257, 1900 La Plata, Argentina
c  Cátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, UNLP, Calles 60 y 119, 1900 La Plata, Argentina
,
María V. Mirífico*
a  Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA, CCT La Plata-CONICET), Facultad de Ciencias Exactas, Departamento de Química, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal 4, 1900 La Plata, Argentina
d  Departamento de Ingeniería Química, Facultad de Ingeniería, Universidad Nacional de La Plata, Calle 47 y 1, 1900 La Plata, Argentina   eMail: mirifi@inifta.unlp.edu.ar
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Publikationsverlauf

Received: 08. September 2015

Accepted after revision: 14. Januar 2016

Publikationsdatum:
09. März 2016 (online)


Abstract

We report a study of the solvent-free condensation reaction of 1,2-dicarbonyl compounds with sulfamide catalyzed by a Keggin-type acid (H3PMo12O40·nH2O, MPA) to obtain 3,4-disubstituted 1,2,5-thiadiazole 1,1-dioxide derivatives. Some reactions were also performed in solution or using nano-sized silica-supported MPA catalyst in order to compare the results under different experimental conditions. Effects of the temperature used for the thermal pretreatment of the catalyst, the reaction temperature, the molar ratios sulfamide/1,2-dicarbonyl compound and MPA/1,2-dicarbonyl compound, and alternative experimental procedures on the yield of the reaction product were investigated. Under suitable experimental conditions eight compounds were obtained in good yields. The catalyst was recycled and reused, but with some loss of its catalytic activity. The presented synthetic method is a simple, clean, and environmentally friendly alternative for synthesizing different 1,2,5-thiadiazole 1,1-dioxide derivatives.

Supporting Information

 
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