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. 2021 Apr 19;26(8):2378.
doi: 10.3390/molecules26082378.

Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone®

Paola S Hellwig  1 , Jonatan S Guedes  1 , Angelita M Barcellos  1 , Gelson Perin  1 , Eder J Lenardão  1
Affiliations

Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone®

Paola S Hellwig et al. Molecules. .

Abstract

We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylselanyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-endo-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organoselenium species, generated in situ through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone® as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80 °C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40-78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15-80%).

Keywords: 1,3-diynes; electrophilic cyclization; heterocycle; organoselenium; selenophene.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Previously reported methods for the synthesis of selenophenes and derivatives (a–c) and our general protocol for the synthesis of selenophenes promoted by Oxone® (d).
Scheme 2
Scheme 2
Reactions in the presence of radical scavenger hydroquinone and TEMPO.
Scheme 3
Scheme 3
Plausible mechanism for the synthesis of 3c and 4h.
See this image and copyright information in PMC

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References

    1. Wiles J.A., Phadke A.S., Bradbury B.J., Pucci M.J., Thanassi J.A., Deshpande M. Selenophene-Containing Inhibitors of Type IIA Bacterial Topoisomerases. J. Med. Chem. 2011;54:3418–3425. doi: 10.1021/jm2002124. - DOI - PubMed
    1. Wilhelm E.A., Jesse C.R., Bortolatto C.F., Nogueira C.W., Savegnago L. Anticonvulsant and Antioxidant Effects of 3-Alkynyl Selenophene in 21-Day-old Rats on Pilocarpine Model of Seizures. Brain Res. Bull. 2009;79:281–287. doi: 10.1016/j.brainresbull.2009.03.006. - DOI - PubMed
    1. Wilhelm E.A., Gai B.M., Souza A.C.G., Bortolatto C.F., Roehrs J.A., Nogueira C.W. Involvement of GABAergic and Glutamatergic Systems in the Anticonvulsant Activity of 3-Alkynyl Selenophene in 21 Day-old Rats. Mol. Cell. Biochem. 2012;365:175–180. doi: 10.1007/s11010-012-1257-3. - DOI - PubMed
    1. Gai B.M., Prigol M., Stein A.L., Nogueira C.W. Antidepressant-like Pharmacological Profile of 3-(4-Fluorophenylselenyl)-2,5-diphenylselenophene: Involvement of Serotonergic System. Neuropharmacology. 2010;59:172–179. doi: 10.1016/j.neuropharm.2010.05.003. - DOI - PubMed
    1. Gai B.M., Stein A.L., Roehrs J.A., Bilheri F.N., Nogueira C.W., Zeni G. Synthesis and Antidepressant-like Activity of Selenophenes Obtained via Iron(III)–PhSeSePh-mediated Cyclization of Z-Selenoenynes. Org. Biomol. Chem. 2012;10:798–807. doi: 10.1039/C1OB06548C. - DOI - PubMed

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