Synthesis 2020; 52(11): 1643-1658
DOI: 10.1055/s-0039-1690800
paper
© Georg Thieme Verlag Stuttgart · New York

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[b][1,4]-oxaselenines Formation from Selenocyanates

María N. Chao
a   Departamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina   Email: jbr@qo.fcen.uba.ar
,
Sergio H. Szajnman
a   Departamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina   Email: jbr@qo.fcen.uba.ar
,
Mauricio Cattaneo
b   INQUINOA-UNT-CONICET, Instituto de Química Física, Facultad de Bioquímica, Química y Farmacia Universidad Nacional de Tucumán, Ayacucho 471, T4000INI, San Miguel de Tucumán, Argentina
,
Jonathan Sanchez Gonzalez
a   Departamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina   Email: jbr@qo.fcen.uba.ar
,
Sergio M. Bonesi
c   Departamento de Química Orgánica and CIHIDECAR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina
,
Juan B. Rodriguez
a   Departamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina   Email: jbr@qo.fcen.uba.ar
› Author Affiliations
This work was supported by grants from Consejo Nacional de Investigaciones Científicas y Técnicas (PIP 112-201501-00631CO) to J.B.R., Agencia Nacional de Promoción Científica y Tecnológica (PICT 2015 No 1349) to J.B.R. and (PICT 2016 No 3224) to M.C., and Universidad de Buenos Aires (20020170100067BA) to J.B.R.
Further Information

Publication History

Received: 09 December 2019

Accepted after revision: 29 December 2019

Publication Date:
17 February 2020 (online)


Abstract

An expedient preparation of selenium-containing hetero­cycles via an m-chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.

Supporting Information

 
  • References

  • 1 Lachkar D, Boudet C, Guinchard X, Crich D. Can. J. Chem. 2012; 90: 944
  • 2 Cao Y, Jiang L, Yi W. Adv. Synth. Catal. 2019; 361: 4360
  • 3 Guram AS. Synlett 1993; 259
  • 4 Potash S, Rozen S. J. Org. Chem. 2014; 79: 11205
  • 5 Garud DR, Koketsu M, Ishihara H. Molecules 2007; 12: 504
  • 6 Modak A, Pinter EN, Cook SP. J. Am. Chem. Soc. 2019; 141: 18405
  • 7 Wei W, Liao L, Qin T, Zhao X. Org. Lett. 2019; 21: 7846
  • 8 Dey A, Hajra A. J. Org. Chem. 2019; 84: 14904
  • 9 Sommen GL, Linden A, Heimgartner H. Tetrahedron 2006; 62: 3344
  • 10 Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
  • 11 Sun L, Yuan Y, Yao M, Wang H, Wang D, Gao M, Chen Y.-H, Aiwen L. Org. Lett. 2019; 21: 1297
  • 12 May SW. Top. Med. Chem. 2016; 17: 87
  • 13 Zaragoza F. Angew. Chem. Int. Ed. 2000; 39: 2077
  • 14 Capper MJ, Wright GS. A, Barbieri L, Luchinat E, Mercatelli E, McAlary L, Yerbury JJ, O’Neill PM, Antonyuk SV, Banci L, Hasnain SS. Nat. Commun. 2018; 9: 1693
  • 15 Macegoniuk K, Grela E, Palus J, Rudzińska E, Grabowiecka A, Biernat M, Berlicki Ł. J. Med. Chem. 2016; 59: 8125
  • 16 Chao MN, Storey M, Li C, Rodríguez MG, Di Salvo F, Szajnman SH, Moreno SN. J, Docampo R, Rodriguez JB. Bioorg. Med. Chem. 2017; 25: 6435
  • 17 Baquedano Y, Nguewa P, Moreno E, Espuelas S, Palop JA, Plano D. Antimicrob. Agents Chemother. 2016; 60: 3802
  • 18 Martín-Montes A, Plano D, Martín-Escolano R, Alcolea V, Díaz M, Pérez-Silanes S, Espuelas S, Moreno E, Marín C, Gutiérrez-Sánchez R, Sanmartín C, Sánchez-Moreno M. Antimicrob. Agents Chemother. 2017; 61: e02546-16
  • 19 Plano D, Karelia DN, Pandey MK, Spallholz JE, Amin S, Sharma AK. J. Med. Chem. 2016; 59: 1946
  • 20 Bouchet LM, Argüello JE. J. Org. Chem. 2018; 83: 5674
  • 21 Kodama S, Saeki T, Mihara K, Higashimae S, Kawaguchi SI, Sonoda M, Nomoto A, Ogawa A. J. Org. Chem. 2017; 82: 12477
  • 22 Chen J, Wang T, Wang T, Lin A, Yaoa H, Xu J. Org. Chem. Front. 2017; 4: 130
  • 23 Rathore V, Upadhyay A, Kumar S. Org. Lett. 2018; 20: 6274
  • 24 Elsherbini M, Hamama WS, Zoorob HH. Coord. Chem. Rev. 2017; 330: 110
  • 25 Elsherbini M, Hamama WS, Zoorob HH. Coord. Chem. Rev. 2016; 312: 149
  • 26 Potapov VA, Musalov MV, Musalova MV, Amosova S. Curr. Org. Chem. 2016; 20: 136
  • 27 Boerma-Markerink MA, Jagt JC, Meyer H, Wildeman J, Van Leusen AM. Synth. Commun. 1975; 5: 147
  • 28 Thompson MC, Turner EE. J. Chem. Soc. 1938; 29
  • 29 Musalov MV, Potapov VA, Musalova MV, Amosova SV. Russ. Chem. Bull. Int. Ed. 2010; 60: 767
  • 30 Potapov VA, Musalov MV, Amosova SV. Tetrahedron Lett. 2011; 52: 4606
  • 31 Musalov MV, Yakimov VA, Potapov VA, Amosova SV, Borodina TN, Zinchenko SV. New J. Chem. 2019; 43: 18476
  • 32 Xu J, Yu X, Yan J, Song Q. Org. Lett. 2017; 19: 6292
  • 33 Maity P, Paroi B, Ranu BC. Org. Lett. 2017; 19: 5748
  • 34 Cinque GM, Szajnman SH, Zhong L, Docampo R, Schvartzapel AJ, Rodriguez JB, Gros EG. J. Med. Chem. 1998; 41: 1540
  • 35 Desmonts G, Couvreur J. N. Engl. J. Med. 1974; 290: 1110
  • 36 Ganguly N, Sukai AK, De S. Synth. Commun. 2001; 31: 301
  • 37 Yang X, Xi C, Jiang Y. Tetrahedron Lett. 2005; 46: 8781
  • 38 Peterson JR, Do HD, Dunham AJ. Can. J. Chem. 1988; 66: 1670
  • 39 Chao MN, Ocampo MV. L, Szajnman SH, Docampo R, Rodriguez JB. Bioorg. Med. Chem. 2019; 27: 1350
  • 40 Glenadel Q, Ayad C, Elia MD, Billard T. J. Fluorine Chem. 2018; 210: 112
  • 41 Bowman WR, Storey JM. D. Chem. Soc. Rev. 2007; 36: 1803
  • 42 Quiclet-Sire B, Zard SZ. Chem. Eur. J. 2006; 12: 6002
  • 43 Armstrong DA, Huie RE, Lymar S, Koppenol WH, Merényi G, Neta P, Stanbury DM, Steenken S, Wardman P. Bioinorg. React. Mech. 2013; 9: 59
  • 44 Lin J.-P, Zhang F.-H, Long Y.-Q. Org. Lett. 2014; 16: 2822
  • 45 Dean JA. Lange’s Handbook of Chemistry, 15th ed. McGraw-Hill; New York: 1998
  • 46 Chao MN, Li C, Storey M, Falcone BN, Szajnman SH, Bonesi SM, Docampo R, Moreno SN. J, Rodriguez JB. ChemMedChem 2016; 11: 2690
  • 47 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA. Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM. W, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision B. 02 . Gaussian, Inc; Wallingford CT: 2004
  • 48 Becke AD. J. Chem. Phys. 1993; 98: 5648
  • 49 Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785
  • 50 Krishnan R, Binkley JS, Seeger R, Pople JA. J. Chem. Phys. 1980; 72: 650
  • 51 Hay PJ, Wadt WR. J. Chem. Phys. 1985; 82: 270
  • 52 Barone V, Cossi M. J. Phys. Chem. A 1998; 102: 1995
  • 53 O’Boyle NM, Tenderholt AL, Langner KM. J. Comp. Chem. 2008; 29: 839
  • 54 Stokes BJ, Opra SM, Sigman MS. J. Am. Chem. Soc. 2012; 134: 11408
  • 55 Shenouda H, Alexanian EJ. Org. Lett. 2019; 21: 9268