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Synthesis 2023; 55(05): 799-807
DOI: 10.1055/a-1958-4406
paper

Pd-G3 XantPhos Mediated Approach to Bis-arylsulfenyl-benzo-2,1,3-thiadiazoles under Microwave Irradiation in DMF: Synthesis and Fluorescent Properties

Ramesh Katla  ∗
a   Organic Chemistry Laboratory-IV, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil
,
Rakhi Katla 
b   Organic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados-UFGD, Dourados/MS, Brazil
,
Eliézer Quadro Oreste
c   Laboratory of Applied and Technological Physical Chemistry, School of Chemistry and Food, Federal University of Rio Grande, Av. Itália, km 8, Rio Grande, RS, Brazil
,
Felipe Kessler
c   Laboratory of Applied and Technological Physical Chemistry, School of Chemistry and Food, Federal University of Rio Grande, Av. Itália, km 8, Rio Grande, RS, Brazil
› Author AffiliationsR.K. is thankful for a ‘CNPq-TWAS fellow’ position. R.K. (Foreign Visiting Professor-Edital N. 03/2020 PROPESP/FURG) thanks Pró-Reitoria de Pesquisa e Pós-Graduação-Federal University of Rio Grande (PROPESP-FURG), Rio Grande-RS for a Visiting Professorship.
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Abstract

Synthesis of bis-arylsulfenyl-benzo-2,1,3-thiadiazoles was accomplished using a Pd-G3 XantPhos as a simple and inexpensive catalyst. Numerous benzene thiols reacted well with 4,7-dibromo-benzo-2,1,3-thiadiazole in DMF, using K2CO3 as the base, obtaining high product yields in a short reaction time. All the synthesized compounds showed remarkable fluorescence properties with emission wavelengths in the visible range. Due to their unique properties, these compounds have potential for application as image probes in fluorescence microscopy. The study found that these compounds have a wide range of potential uses in the area of sensors, as well as displaying other useful photophysical properties.

Key words

cross-coupling - XantPhos-PdG3 - MWI - DMF - photophysical properties - homogeneous catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1958-4406
  • Supporting Information


Publication History

Received: 14 July 2022

Accepted after revision: 11 October 2022

Accepted Manuscript online:
11 October 2022

Article published online:
09 November 2022

© 2022. Thieme. All rights reserved

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  • References

    • 1a Gangjee A, Zeng Y, Talreja T, McGuire JJ, Kisliuk RL, Queener SF. J. Med. Chem. 2007; 50: 3046
      CrossrefPubMed
    • 1b Hu W, Guo Z, Chu F, Bai A, Yi X, Cheng G, Li J. Bioorg. Med. Chem. Lett. 2003; 13: 1153
      CrossrefPubMed
    • 1c Caboni P, Sammelson RE, Casida JE. J. Agric. Food Chem. 2003; 24: 7055
      CrossrefPubMed
    • 1d Wang Y, Chackalamannil S, Hu Z, Clader ZW, Greenlee W, Billard W, Binch HI. I. I, Crosby G, Ruperto V, Duffy RA, McQuade R, Lachowicz J. Bioorg. Med. Chem. Lett. 2000; 10: 2247
      CrossrefPubMed
    • 1e Nielson SF, Nielson EO, Olsen GM, Liljefors T, Peters D. J. Med. Chem. 2000; 43: 2217
      CrossrefPubMed
    • 1f De Martino G, Edler MC, La Regina G, Cosuccia A, Barbera MC, Barrow D, Nicholson RI, Chiosis G, Brancale A, Hamel E, Artico M, Silvestri R. J. Med. Chem. 2006; 49: 947
      CrossrefPubMed
    • 2a Metzner P, Thuillier A. In Sulfur Reagents in Organic Synthesis . Katritzky AR, MethCohn O, Rees CW. Academic Press; San Diego: 1994
      Google Scholar
    • 2b Kondo T, Mitsudo T. Chem. Rev. 2000; 100: 3205
      CrossrefPubMed
    • 2c Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
      CrossrefPubMed
  • 3 Kabir MS, Lorenz M, Van Linn ML, Namjoshi OA, Ara S, Cook JM. J. Org. Chem. 2010; 75: 3626
    CrossrefPubMed
    • 4a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
      CrossrefPubMed
    • 4b Ananikov VP, Zalesskiy SS, Beletskaya IP. Curr. Org. Synth. 2011; 8: 2
      Crossref
  • 5 Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
    CrossrefPubMed
    • 6a Neto BA. D, Lapis AA. M, da Silva EN. Jr, Dupont J. Eur. J. Org. Chem. 2012; 228
    • 6b Kato S, Matsumoto T, Ishi-i T, Thiemann T, Shigeiwa M, Gorohmaru H, Maeda S, Yamashita Y, Mataka S. Chem. Commun. 2004; 2342
      CrossrefPubMed
    • 7a Thomas KR. J, Velusamy M, Lin JT, Sun SS, Tao YT, Chuen CH. Chem. Commun. 2004; 2328
      CrossrefPubMed
    • 7b Thomas KR. J, Lin JT, Velusamy M, Tao YT, Chuen CH. Adv. Funct. Mater. 2004; 14: 83
      Crossref
    • 8a Mataka S, Takahashi K, Imura T, Tashiro M. J. Heterocycl. Chem. 1982; 19: 1481
      Crossref
    • 8b Gozzo F. J. Agric. Food Chem. 2003; 51: 4487
      CrossrefPubMed
    • 8c Balasankar T, Gopalakrishnan M, Nagarajan S. Eur. J. Med. Chem. 2005; 40: 728
      CrossrefPubMed
  • 9 Neto BA. D, Carvalho PH. P. R, Correa JR. Acc. Chem. Res. 2015; 48: 1560
    CrossrefPubMed
  • 10 dos Santos BF, Pereira CF, Pinz MP, Oliveira AR, Brand G, Katla R, Domingues NL. C. Appl. Organomet. Chem. 2020; e5650
    CrossrefPubMed
  • 11 Kukreja G, Phukan S, Kodam J, More DM, Uravane MV, Palle VP, Kamboj RK. WO2013005157 A1, 2013
    PubMed
  • 12 Balaguez RA, Ricordi VG, Duarte RC, Toldo JM, Santos CM, Schneider PH, Gonçalves PF. B, Rodembusch FS, Alves D. RSC Adv. 2016; 6: 49613
    CrossrefPubMed
  • 13 Yamashita Y, One K, Tomura M, Tanaka S. Tetrahedron 1997; 53: 10169
    CrossrefPubMed
    • 14a Katla R, Katla R, da Silva CD. G, dos Santos BF, Branquinho TA, Ferro CT. B, Domingues NL. C. ChemistrySelect 2019; 4: 1
      CrossrefPubMed
    • 14b de Oliveira AR, da Silva CD. G, Katla R, Rocha MP. D, Albuquerque TB, Kupfer VL, Rinaldi AW, Domingues NL. C. ChemistrySelect 2017; 2: 4462
      Crossref
    • 14c Katla R, Chowrasia R, da Silva CD. G, de Oliveira AR, dos Santos BF, Domingues NL. C. Synthesis 2017; 5143
    • 14d Katla R, Chowrasia R, Manjari PS, da Silva CD. G, dos Santos BF, Domingues NL. C. New J. Chem. 2016; 40: 9471
      Crossref
    • 14e Chowrasia R, Katla R, Rocha MP. D, Branquinho TA, de Oliveira AR, Manjari PS, Domingues NL. C. Tetrahedron Lett. 2016; 57: 1656
      Crossref
    • 14f de Oliveira AR, Katla R, Rocha MP. D, Albuquerque TB, da Silva CD. G, Kupfer VL, Rinaldi AW, Domingues NL. C. Synthesis 2016; 4489
    • 14g Katla R, Katla R, Domingues NL. C. ChemistrySelect 2022; 7: e202200582
      Crossref
  • 15 Katla R, Katla R, Domingues NL. C. Synthesis 2022; 54: 4608
    Article in Thieme ConnectPubMed
    • 16a Nogueira CW, Rocha JB. T. The Chemistry of Organic Selenium and Tellurium Compounds. In Patai’s Chemistry of Functional Groups, Vol. 3. Rappoport Z. Wiley; Chichester: 2011
      Google Scholar
    • 16b Carland M, Fenner T. The Use of Selenium-Based Drugs in Medicine. In Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. Gielen M, Ticking ER. T. Wiley; Chichester: 2005
      Google Scholar
    • 17a Kim HS, Kim YJ, Lee H, Park KY, Lee C, Chin CS. Angew. Chem. Int. Ed. 2002; 41: 4300
      CrossrefPubMed
    • 17b Lenardão EJ, Feijó S, Thurow JO, Perin G, Jacob RG, Silveira CC. Tetrahedron Lett. 2009; 50: 5215
      Crossref
    • 17c Lenardão EJ, Borges EL, Mendes SR, Perin G, Jacob RG. Tetrahedron Lett. 2008; 49: 1919
      Crossref
    • 17d Thurow S, Pereira VA, Martinez DM, Alves D, Perin G, Jacob RG, Lenardão EJ. Tetrahedron Lett. 2011; 52: 640
      Crossref
    • 17e Alberto EE, Rossato LL, Alves SH, Alves D, Braga AL. Org. Biomol. Chem. 2011; 9: 1001
      CrossrefPubMed
    • 18a Rampon DS, Rodembusch FS, Schneider JM. F. M, Bechtold IH, Gonçalves PF. B, Merlo A, Schneider PH. J. Mater. Chem. 2010; 20: 715
      Crossref
    • 18b Samb I, Bell J, Toullec PY, Michelet V, Leray I. Org. Lett. 2011; 13: 1182
      CrossrefPubMed
    • 18c Goswami S, Hazra A, Chakrabarty R, Fun HK. Org. Lett. 2009; 11: 4350
      CrossrefPubMed
    • 18d Tang B, Xing Y, Li P, Zhang N, Yu F, Yang G. J. Am. Chem. Soc. 2007; 129: 11666
      CrossrefPubMed
    • 19a Vieira AA, Cristiano R, Bortoluzzi AJ, Gallardo H. J. Mol. Struct. 2008; 875: 364
      Crossref
    • 19b Moro AV, Ferreira PC, Migowski P, Rodembusch FS, Dupont J, Lüdtke DS. Tetrahedron 2013; 69: 201
      Crossref
  • 20 Frizon TE. A, Valdivia JC. M, Westrup JL, Duarte RC, Zapp E, Domiciano KG, Rodembusch FS, Dal-Bó AG. Dyes Pigm. 2016; 135: 26
    CrossrefPubMed
  • 21 Benevides TO, Regis E, Nicoleti CR, Bechtold IH, Vieira AA. Dyes Pigm. 2019; 163: 300
    CrossrefPubMed
  • 22 Tao YM, Li HY, Xu QL, Zhu YC, Kang LC, Zheng YX, Zuo JL, You XZ. Synth. Met. 2011; 161: 718
    Crossref
  • 23 Oliveira FF. D, Santos DC. B. D, Lapis AA. M, Corrêa JR, Gomes AF, Gozzo FC, Moreira PF. Jr, Oliveira VC, Quina FH, Neto BA. D. Bioorg. Med. Chem. Lett. 2010; 20: 6001
    CrossrefPubMed
  • 24 Gudim NS, Knyazeva EA, Mikhalchenko LV, Golovanov IS, Popov VV, Obruchnikova NV, Rakitin OA. Molecules 2021; 26: 4931
    CrossrefPubMed
  • 25 Roig B, Chalmin E, Touraud E, Thomas O. Talanta 2002; 56: 585
    CrossrefPubMed
  • 26 Hao Y, Yin Q, Zhang Y, Xu M, Chen S. Molecules 2019; 24: 3716
    CrossrefPubMed