Synthesis 2019; 51(02): 578-586
DOI: 10.1055/s-0037-1610656
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-(Arylselanyl)benzo[b]chalcogenophenes via Intramolecular Cyclization of Vinyl Selenides

Guilherme Stach
a   Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: lenardao@ufpel.edu.br   Email: gelson_perin@ufpel.edu.br
,
Thiago J. Peglow
a   Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: lenardao@ufpel.edu.br   Email: gelson_perin@ufpel.edu.br
,
Juliano A. Roehrs
b   Instituto Federal de Educação Ciência e Tecnologia Sul-rio-grandense – IFSul, 96015-360, Pelotas, RS, Brazil
,
Filipe Penteado
a   Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: lenardao@ufpel.edu.br   Email: gelson_perin@ufpel.edu.br
,
Thiago Barcellos
c   Laboratório de Biotecnologia de Produtos Naturais e Sintéticos - Universidade de Caxias do Sul – UCS, Caxias do Sul, RS, Brazil
,
Raquel G. Jacob
a   Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: lenardao@ufpel.edu.br   Email: gelson_perin@ufpel.edu.br
,
a   Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: lenardao@ufpel.edu.br   Email: gelson_perin@ufpel.edu.br
,
Gelson Perin*
a   Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: lenardao@ufpel.edu.br   Email: gelson_perin@ufpel.edu.br
› Author Affiliations
This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) – Finance Code 001. CNPq, FAPERGS and FINEP are thanked for financial support.
Further Information

Publication History

Received: 04 July 2018

Accepted after revision: 23 August 2018

Publication Date:
19 September 2018 (online)


Abstract

An efficient protocol to access 2-arylselanylbenzo[b]chalcogenophene derivatives through the Cu(I)-catalyzed annulation of vinyl selenides is described. The key vinyl selenides were easily prepared from properly functionalized 1,1-dibromostyrenes and the method allowed the synthesis of 2-arylselanylfurans, -thiophenes, and -selenophenes in moderate to excellent yields.

Supporting Information

 
  • References

    • 1a Quin LD. Tyrell JA. Fundamentals of Heterocyclic Chemistry . Wiley-VCH; Weinheim: 2010
    • 1b Alvarez-Builla J. Vaquero JJ. Barluenga J. Modern Heterocyclic Chemistry . Wiley-VCH; Weinheim: 2010
    • 1c Comprehensive Heterocyclic Chemistry III . Vol 1. Katritsky AR. Rees CW. Scriven EF. Pergamon; Oxford: 1999
    • 1d Gomtsyan A. Chem. Heterocycl. Comp. 2012; 48: 7
    • 1e Horton DA. Bourne GT. Smythe ML. Chem. Rev. 2003; 103: 893
    • 2a McCallion GD. Curr. Org. Chem. 1999; 3: 67
    • 2b Lipshutz BH. Chem. Rev. 1986; 86: 795
    • 3a Navarro E. Alonso SJ. Trujillo J. Jorge E. Pérez C. J. Nat. Prod. 2001; 64: 134
    • 3b Kraus GA. Kim I. Org. Lett. 2003; 5: 1191
    • 3c Lu H. Liu G.-T. Planta Med. 1992; 58: 311
    • 3d Sun M. Zhao C. Gfesser GA. Thiffault C. Miller TR. Marsh K. Wetter J. Curtis M. Faghih R. Esbenshade TA. Hancock AA. Cowart M. J. Med. Chem. 2005; 48: 6482
    • 3e Inoue M. Carson MW. Frontier AJ. Danishefsky SJ. J. Am. Chem. Soc. 2001; 123: 1878
    • 3f Dixit M. Tripathi BK. Tamrakar AK. Srivastava AK. Kumar B. Goel A. Bioorg. Med. Chem. 2007; 15: 727
    • 3g Ando K. Kawamura Y. Akai Y. Kunitomo J. Yokomizo T. Yamashita M. Ohta S. Ohishi T. Ohishi Y. Org. Biomol. Chem. 2008; 6: 296
    • 3h Schultz DM. Prescher JA. Kidd S. Marona-Lewicka D. Nichols DE. Monte A. Bioorg. Med. Chem. 2008; 16: 6242
    • 4a Rossi A. Pergola C. Koeberle A. Hoffmann M. Dehm F. Bramanti P. Cuzzocrea S. Werz O. Sautebin L. Br. J. Pharmacol. 2010; 161: 555
    • 4b Chen J.-H. Chang Y.-C. Chang D. Wang Y.-T. Nie K. Chang R.-F. Nalcioglu O. Huang C.-S. Su M.-Y. Magn. Reson. Imaging 2011; 29: 91
    • 5a Flynn BL. Hamel E. Jung MK. J. Med. Chem. 2002; 45: 2670
    • 5b Liu H. Liu J. van Breemen RB. Thatcher GR. J. Bolton JL. Chem. Res. Toxicol. 2005; 18: 162
  • 6 Pinney KG. Bounds AD. Dingeman KM. Mocharla VP. Pettit GR. Bai R. Hamel E. Bioorg. Med. Chem. Lett. 1999; 9: 1081
    • 7a Flynn BL. Flynn GP. Hamel E. Jung MK. Bioorg. Med. Chem. Lett. 2001; 11: 2341
    • 7b Flynn BL. Hamel E. Jung MK. J. Med. Chem. 2002; 45: 2670
  • 8 Salimbeni A. Canevotti R. Paleari F. Poma D. Caliari S. Fici F. Cirillo R. Renzetti AR. Subissi A. Belvisi L. Bravi G. Scolastico C. Giachetti A. J. Med. Chem. 1995; 38: 4806
    • 9a Weinstock J. Keenan RM. Samanen J. Hempel J. Finkelstein JA. Franz RG. Gaitanopoulos DE. Girard GR. Gleason JG. Hill DT. Morgan TM. Peishoff CE. Aiyar N. Brooks DP. Fredrickson TA. Ohlstein EH. Ruffolo RR. Stack EJ. Sulpizio AC. Weidley EF. Edwards RM. J. Med. Chem. 1991; 34: 1514
    • 9b Robins GW. Scott LJ. Drugs 2005; 65: 2355
    • 10a Grange RL. Ziogas J. Angus JA. Schiesser CH. Tetrahedron Lett. 2007; 48: 6301
    • 10b Grange RL. Ziogas J. North AJ. Angus JA. Schiesser CH. Bioorg. Med. Chem. Lett. 2008; 18: 1241
    • 10c Staples MK. Grange RL. Angus JA. Ziogas J. Tan NP. H. Taylor MK. Schiesser CH. Org. Biomol. Chem. 2011; 9: 473
    • 10d Giarrusso MA. Taylor MK. Ziogas J. Brody KM. Macdougall PE. Schiesser CH. Asian J. Org. Chem. 2012; 1: 274
    • 11a Vieira BM. Thurow S. da Costa M. Casaril AM. Domingues M. Schumacher RF. Perin G. Alves D. Savegnago L. Lenardão EJ. Asian J. Org. Chem. 2017; 6: 1635
    • 11b Savegnago L. Vieira AI. Seus N. Goldani B. Castro MR. Lenardão EJ. Alves D. Tetrahedron Lett. 2013; 54: 40
    • 12a Wen Z. Xu J. Wang Z. Qi H. Xu Q. Bai Z. Zhang Q. Bao K. Wu Y. Zhang W. Eur. J. Med. Chem. 2015; 90: 184
    • 12b Wen Z. Li X. Zuo D. Lang B. Wu Y. Jiang M. Ma H. Bao K. Wu Y. Zhang W. Sci. Rep. 2016; 6: 23986
  • 13 Hamdouchi C. Blas J. Prado M. Gruber J. Heinz BA. Vance L. J. Med. Chem. 1999; 42: 50
  • 14 Bochis RJ. Olen LE. Fisher MH. Reamer RA. J. Med. Chem. 1981; 24: 1483
  • 15 Manarin F. Roehrs JA. Gay RM. Brandão R. Menezes PH. Nogueira CW. Zeni G. J. Org. Chem. 2009; 74: 2153
  • 16 Liu J. Chen W. Wang L. RSC Adv. 2013; 3: 4723
  • 17 Perin G. Roehrs JA. Hellwig PS. Stach G. Barcellos T. Lenardão EJ. Jacob RG. Luz EQ. ChemistrySelect 2017; 2: 4561
    • 18a Chelucci G. Chem. Rev. 2012; 112: 1344
    • 18b Liu J. Zhang X. Shi L. Liu M. Yue Y. Li F. Zhuo K. Chem. Commun. 2014; 50: 9887
    • 18c Chai DI. Lautens M. J. Org. Chem. 2009; 74: 3054
    • 18d Jouvin K. Coste A. Bayle A. Legrand F. Karthikeyan G. Tadiparthi K. Evano G. Organometallics 2012; 31: 7933
  • 19 Webber R. Peglow TJ. Nobre PC. Barcellos AM. Roehrs JA. Schumacher RF. Perin G. Tetrahedron Lett. 2016; 57: 4128
    • 20a Nagamochi M. Fang Y.-Q. Lautens M. Org. Lett. 2007; 9: 2955
    • 20b Newman SG. Aureggi V. Bryan CS. Lautens M. Chem. Commun. 2009; 5236
    • 20c Bilheri FN. Pistoia RP. Back DF. Zeni G. Adv. Synth. Catal. 2017; 359: 4208
  • 21 Huh DH. Jeong JS. Lee HB. Ryu H. Kim YG. Tetrahedron 2002; 58: 9925