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

Nelson Rodríguez Arroyo; María F. Rozas; Patricia Vázquez; Gustavo P. Romanelli; María V. Mirífico

doi:10.1055/s-0035-1561371

Synthesis, Table of Contents

Synthesis 2016; 48(09): 1344-1352
DOI: 10.1055/s-0035-1561371

paper

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

Nelson Rodríguez Arroyo

^aInstituto 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

^aInstituto 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

^bCentro 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

^bCentro 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

^cCátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, UNLP, Calles 60 y 119, 1900 La Plata, Argentina

,

María V. Mirífico*

^aInstituto 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

^dDepartamento 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

› Author Affiliations

Abstract

All articles of this category

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.

Key words

heterocycles - solvent-free reaction - condensation - acid catalysis - heteropolyacids - 1,2-dicarbonyl compounds - sulfamide

Full Text

References

References
1 Gazieva GA, Kravchenko AN, Lebedev OV. Russ. Chem. Rev. 2000; 69: 221
2 Clerici F. Adv. Heterocycl. Chem. 2002; 83: 71
3 Robichaud AJ. Curr. Top. Med. Chem. 2006; 6: 553
4 Dungan LB, Rowley EG, Dixson JA, Ali SF, Crawford SD, Sehgel S, Whiteside MP, Zydowsky TM, Yeager WH. PCT Int. Appl. WO 6858, 2005 ; Chem. Abstr. 2005, 142, 150261.
5 Linder T, Badiola V, Baumgartner T, Sutherland TC. Org. Lett. 2010; 12: 4520
6 Grillo CA, Mirífico MV, Morales ML, Reigosa MA, Fernández Lorenzo de Mele M. J. Hazard. Mater. 2009; 170: 1173
7 Banera MJ, Caram JA, Gervasi CA, Mirífico MV. J. Appl. Electrochem. 2014; 44: 1337
8 Mirífico MV, Caram JA, Gennaro AM, Cobos CJ, Vasini EJ. J. Phys. Org. Chem. 2009; 22: 964
9 Mirífico MV, Caram JA, Gennaro AM, Cobos CJ, Vasini EJ. J. Phys. Org. Chem. 2011; 24: 1039
10 Lee C-H, Korp JD, Kohn H. J. Org. Chem. 1989; 54: 3077
11 Esser T, Karu AE, Toia RF, Casida JE. Chem. Res. Toxicol. 1991; 4: 162
12 Alberola A, Andres JM, Gonzalez A, Pedrosa R, Vicente M. Synthesis 1991; 355
13 Wright JB. J. Org. Chem. 1964; 29: 1905
14 Koutentis PA In Comprehensive Heterocyclic Chemistry III . Vol. 5. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Oxford: 2008: 516
15 Xie Y, Shuku Y, Matsushita MM, Awaga K. Chem. Commun. 2014; 50: 4178
16 Schüttler C, Li-Böhmer Z, Harms K, von Zezschwitz P. Org. Lett. 2013; 15: 800
17 Erturk AG, Bekdemir Y. Phosphorus, Sulfur Silicon Relat. Elem. 2014; 189: 285
18 Bennardi DO, Romanelli GP, Sathicq AG, Autino JC, Baronetti GT, Thomas HJ. Appl. Catal., A 2011; 404: 68
19 Heravi M, Sadjadi S. J. Iran. Chem. Soc. 2009; 6: 1
20 Romanelli GP, Autino JC. Mini-Rev. Org. Chem. 2009; 6: 359
21 Firouzabadi H, Jafari AA. J. Iran. Chem. Soc. 2005; 2: 85
22 Heravi MM, Derikvand F, Haeri A, Oskoie HA, Bamoharram FF. Synth. Commun. 2008; 38: 135
23 Okuhara T. Catal. Today 2002; 73: 167
24 Mizuno N, Misono V. Curr. Opin. Solid State Mater. Sci. 1997; 2: 84
25 Takana K, Koda F. Chem. Rev. 2000; 100: 1025
26 Rostami M, Khosropour A, Mirkhani V, Moghadam M, Tangestaninejad S, Mohammadpoor-Baltork I. Appl. Catal., A 2011; 397: 27
27 Kozhevnikov I. J. Mol. Catal. A: Chem. 2007; 262: 86
28 Vorreither K, Ziegler E. Monatsh. Chem. 1965; 96: 216
29 Svartman EL, Rozas MF, Piro OE, Castellano EE, Mirífico MV. Synthesis 2006; 2313
30 Svartman EL, Caram JA, Mirífico MV, Vasini EJ. Can. J. Chem. 1999; 77: 511
31 Marcì G, García-López EI, Palmisano L. Eur. J. Inorg. Chem. 2014; 21
32 Armarego WL. F, Perrin DD. Purification of Laboratory Chemicals . 4th ed. Butterworth Heinemann; Oxford: 1997
33 Harris FW, Zhang D, Hu J. J. Org. Chem. 2005; 70: 707
34 Vogel AI. A Textbook of Practical Organic Chemistry . Longmans Green; London: 1948: 679
35 Gomberg M, Van Natta FJ. J. Am. Chem. Soc. 1929; 51: 2238
36 Sheldrick GM. SHELXS-97 Program for Crystal Structure Resolution . University of Göttingen; Germany: 1997
37 Sheldrick GM. SHELXS-97 Program for Crystal Structure Analysis . University of Göttingen; Germany: 1997

Supplementary Material

Supporting Information