Synthesis 2019; 51(11): 2293-2304
DOI: 10.1055/s-0037-1611747
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Organoselanyl-1H-pyrazoles: Oxone®-Mediated Electrophilic Cyclization of α,β-Alkynyl Hydrazones by Using Diorganyl Diselenides

a  Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: gelson_perin@ufpel.edu.br
,
Patrick C. Nobre
a  Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: gelson_perin@ufpel.edu.br
,
Daniela H. Mailahn
a  Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: gelson_perin@ufpel.edu.br
,
Márcio S. Silva
a  Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil   Email: gelson_perin@ufpel.edu.br
,
Thiago Barcellos
b  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: 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: gelson_perin@ufpel.edu.br
,
Claudio Santi
c  Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, Perugia, Italy
,
Juliano A. Roehrs
d  Instituto Federal de Educação Ciência e Tecnologia Sul-rio-grandense, IFSul, 96015360, Pelotas, RS, Brazil
› Author Affiliations
The authors are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS) for financial support (Grant number: 17/2551-0000987-8). This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) (finance Code 001). CNPq is also acknowledged for fellowships to G.P., R.G.J., and E.J.L.
Further Information

Publication History

Received: 17 December 2018

Accepted after revision: 05 February 2019

Publication Date:
14 March 2019 (eFirst)

Abstract

A simple and efficient method for the synthesis of 4‑organoselanyl-1H-pyrazoles has been developed, taking place under metal- and halogen-free conditions. Electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone® in ethanol as solvent in an open-flask at 70 °C. These electrophilic selenium species were employed in the selenylation/cyclization of α,β-alkynyl hydrazones, giving the title compounds in moderate to excellent yields. The final species of selenium obtained from the reaction of diphenyl diselenide with Oxone® were characterized by 77Se NMR spectroscopy and high-resolution mass spectrometry (HRMS).

Supporting Information

 
  • References

    • 2a Karrouchi K, Radi S, Ramli Y, Taoufik J, Mabkhot YN, Al-aizari FA, Ansar M. Molecules 2018; 23: 134
    • 2b Ansari A, Ali A, Asif M. Shamsuzzaman New J. Chem. 2017; 41: 16
    • 2c Faria JV, Vegi PF, Miguita AG. C, dos Santos MS, Boechat N, Bernardino AM. R. Bioorg. Med. Chem. 2017; 25: 5891
    • 2d Khan MF, Alam MM, Verma G, Akhtar W, Akhter M, Shaquiquzzaman M. Eur. J. Med. Chem. 2016; 120: 170
    • 2e Kumar V, Kaur K, Gupta GK, Sharma AK. Eur. J. Med. Chem. 2013; 69: 735
    • 3a Ahn M, Gunasekaran P, Rajasekaran G, Kim EY, Lee S.-J, Bang G, Cho K, Hyun J.-K, Lee H.-J, Jeon YH, Kim N.-H, Ryu EK, Shin SY, Bang JK. Eur. J. Med. Chem. 2017; 125: 551
    • 3b Viveka S, Dinesha Nagaraja GK, Shama P, Basavarajaswamy G, Rao KP, Sreenivasa MY. Med. Chem. Res. 2018; 27: 171
    • 3c Beena KP, Elkhider AA. A, Shebina P, Sindhuja V. J. Chem. Pharm. Res. 2016; 8: 915
    • 4a El Shehry MF, Ghorab MM, Abbas SY, Fayed EA, Shedid SA, Ammar YA. Eur. J. Med. Chem. 2018; 143: 1463
    • 4b Zhang J, Tan D.-J, Wang T, Jing S.-S, Kang Y, Zhang Z.-T. J. Mol. Struct. 2017; 1149: 235
    • 5a Florentino IF, da Silva DP. B, Martins JL. R, da Silva TS, Santos FC. A, Tonussi CR, Vasconcelos GA, Vaz BG, Lião LM, Menegatti R, Costa EA. Inflammopharmacology 2016; 24: 265
    • 5b Domiati S, El-Mallah A, Ghoneim A, Bekhit A, El Razik HA. Inflammopharmacology 2016; 24: 163
    • 6a Banuppriya G, Sribalan R, Padmini V. ChemistrySelect 2017; 2: 9168
    • 6b Nossier ES, Fahmy HH, Khalifa NM, El-Eraky WI, Baset MA. Molecules 2017; 22: 512
  • 7 Tantawy AS, Nasr MN. A, El-Sayed MA. A, Tawfik SS. Med. Chem. Res. 2012; 21: 4139
    • 8a Sravanthi K, Snehalatha P, Subhasini NJ. P. J. Heterocycl. Chem. 2018; 55: 508
    • 8b Chougala BM, Samundeeswari S, Holiyachi M, Shastri LA, Dodamani S, Jalalpure S, Dixit SR, Joshi SD, Sunagar VA. Eur. J. Med. Chem. 2017; 125: 101
    • 9a Verma G, Chashoo G, Ali A, Khan MF, Akhar W, Ali I, Akhtar M, Alam MM, Shaquiquzzaman M. Bioorg. Chem. 2018; 77: 106
    • 9b El-Gaby MS. A, Ghorab MM, Ismail ZH, Abdel-Gawad SM, Aly HM. Med. Chem. Res. 2018; 27: 72
  • 10 McCormack PL. Drugs 2011; 71: 2427
  • 11 Ismail MA. H, Lehamann J, El Ella DA. A, Albohy A, Abouzid KA. M. Med. Chem. Res. 2009; 18: 725
  • 12 Dunn PJ, Galvin S, Hettenbach K. Green Chem. 2004; 6: 43
  • 13 Romero A, Ramos E, Ares I, Castellano V, Martínez M, Martínez-Larrañaga MR, Anadón A, Martínez MA. Toxicol. Lett. 2016; 252: 42
    • 14a Despotopoulou C, Klier L, Knochel P. Org. Lett. 2009; 11: 3326
    • 14b Fustero S, Román R, Sanz-Cervera JF, Simón-Fuentes A, Cuñat AC, Villanova S, Murguía M. J. Org. Chem. 2008; 73: 3523
  • 15 Giornal F, Pazenok S, Rodefeld L, Lui N, Vors J.-P, Leroux FR. J. Fluorine Chem. 2013; 152: 2
  • 16 Hsieh M.-T, Lin H.-C, Kuo SC. Tetrahedron 2016; 72: 5880
    • 17a Janin YL. Chem. Rev. 2012; 112: 3924
    • 17b Fustero S, Sánchez-Roselló M, Barrio P, Simóm-Fuentes A. Chem. Rev. 2011; 111: 6984
    • 17c Aggarwal R, Kumar V, Kumar R, Singh SP. Beilstein J. Org. Chem. 2011; 7: 179
    • 17d Fustero S, Simón-Fuentes A, Sanz-Cervera JF. Org. Prep. Proced. Int. 2009; 41: 253
    • 18a Fu Y, Wang M.-X, Zhang D, Hou Y.-W, Gao S, Zhao L.-X, Ye F. RSC Adv. 2017; 7: 46858
    • 18b da Silva MJ. V, Poletto J, Jacomini AP, Pianoski KE, Gonçalves DS, Ribeiro GM, Melo SM. S, Back DF, Moura S, Rosa FA. J. Org. Chem. 2017; 82: 12590
    • 18c Ekbote SS, Gadge ST, Bhanage BM. Curr. Catal. 2016; 5: 4
    • 18d Schneider Y, Prévost J, Gobin M, Legault CY. Org. Lett. 2014; 16: 596
    • 18e Zhang J, Shao Y, Wang H, Luo Q, Chen J, Xu D, Wan X. Org. Lett. 2014; 16: 3312
    • 18f Nasseri MA, Salimi M, Esmaeili AA. RSC Adv. 2014; 4: 61193
    • 19a Das P, Gondo S, Tokunaga E, Sumii Y, Shibata N. Org. Lett. 2018; 20: 558
    • 19b Remy R, Bochet CG. Eur. J. Chem. 2018; 316
    • 19c Yu Y, Huang W, Chen Y, Gao B, Wu W, Jiang H. Green. Chem. 2016; 18: 6445
    • 19d Zheng Y, Zhang X, Yao R, Wen Y, Huang J, Xu X. J. Org. Chem. 2016; 81: 11072
    • 19e Portillo M, Maxwell MA, Frederich JH. Org. Lett. 2016; 18: 5142
    • 19f Pérez-Aguilar MC, Valdés C. Angew. Chem. Int. Ed. 2015; 54: 13729
    • 19g Decuypere E, Specklin S, Gabillet S, Audisio D, Liu H, Plougastel L, Kolodych S, Taran F. Org. Lett. 2015; 17: 362
    • 19h Specklin S, Decuypere E, Plougastel L, Aliani S, Taran F. J. Org. Chem. 2014; 79: 7772
    • 19i Merchant RR, Allwood DM, Blakemore DC, Ley SV. J. Org. Chem. 2014; 79: 8800
    • 19j Guo H, Zhang D, Zhu C, Li J, Xu G, Sun J. Org. Lett. 2014; 16: 3110
    • 20a Muzalevskiy VM, Rulev AY, Romanov AR, Kondrashov EV, Ushavok IA, Chertkov VA, Nenajdenko VG. J. Org. Chem. 2017; 82: 7200
    • 20b Fricero P, Bialy L, Brown AW, Czechtizky W, Méndez M, Harrity JP. A. J. Org. Chem. 2017; 82: 1688
    • 20c Götzinger AC, TheBeling FA, Hoppe C, Müller TJ. J. J. Org. Chem. 2016; 81: 10328
    • 20d Ding Y, Zhang T, Chen Q.-Y, Zhu C. Org. Lett. 2016; 18: 4206
    • 20e Zang H, Wei Q, Zhu G, Qu J, Wang B. Tetrahedron Lett. 2016; 57: 2633
    • 20f Hsieh M.-T, Kuo S.-C, Lin H.-C. Adv. Synth. Catal. 2015; 357: 683
    • 20g Wang Y, Han J, Chen J, Cao W. Tetrahedron 2015; 71: 8256
    • 20h Zhu C, Bi B, Yao D, Chen Q.-Y, Luo Z.-B. Synthesis 2015; 47: 1877
    • 20i Harigae R, Moriyama K, Togo H. J. Org. Chem. 2014; 79: 2049
    • 20j Zhang X, Kang J, Niu P, Wu J, Yu W, Chang J. J. Org. Chem. 2014; 79: 10170
    • 21a Yang Y, Hu Z.-L, Li R.-H, Chen Y.-H, Zhan Z.-P. Org. Biomol. Chem. 2018; 16: 197
    • 21b Kashiwa M, Kuwata Y, Sonoda M, Tanimori S. Tetrahedron 2016; 72: 304
    • 21c Ji G, Wang X, Zhang S, Xu Y, Ye Y, Li M, Zhang Y, Wang J. Chem. Commun. 2014; 50: 4361
    • 21d Kong Y, Tang M, Wang Y. Org. Lett. 2014; 16: 576
    • 21e Wen J.-J, Tang H.-T, Xiong K, Ding Z.-C, Zhan Z.-P. Org. Lett. 2014; 16: 5940
    • 21f Zhang T, Bao W. J. Org. Chem. 2013; 78: 1317
    • 22a Tang L, Ma M, Zhang Q, Luo H, Wang T, Chai Y. Adv. Synth. Catal. 2017; 359: 2610
    • 22b Orrego-Hernández J, Portilla J. J. Org. Chem. 2017; 82: 13376
    • 22c Fan X.-W, Lei T, Zhou C, Meng Q.-Y, Chen B, Tung C.-H, Wu L.-Z. J. Org. Chem. 2016; 81: 7127
    • 22d Vanjari R, Guntreddi T, Kumar S, Singh KN. Chem. Commun. 2015; 51: 366
    • 22e Mantenuto S, Mantellini F, Favi G, Attanasi OA. Org. Lett. 2015; 17: 2014
    • 22f Guo C, Sahoo B, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2014; 136: 17402
    • 23a Horibe T, Ohmura S, Ishihara K. Org. Lett. 2017; 19: 5525
    • 23b Jing X, Yuan D, Yu L. Adv. Synth. Catal. 2017; 359: 1194
    • 23c Wang T, Jing X, Chen C, Yu L. J. Org. Chem. 2017; 82: 9342
    • 23d Jin W, Zheng P, Wong W.-T, Law G.-L. Adv. Synth. Catal. 2017; 359: 1588
    • 23e Guo R, Huang J, Huang H, Zhao X. Org. Lett. 2016; 18: 504
    • 23f Ortgies S, Depken C, Breder A. Org. Lett. 2016; 18: 2856
    • 23g Wang Y, Yu L, Zhu B, Yu L. J. Mater. Chem. A 2016; 4: 10828
    • 23h Yu L, Bai Z, Zhang X, Zhang X, Ding Y, Xu Q. Catal. Sci. Technol. 2016; 6: 1804
    • 23i Yu L, Chen F, Ding Y. ChemCatChem 2016; 8: 1033
    • 23j Zhang X, Ye J, Yu L, Shi X, Zhang M, Xu Q, Lautens M. Adv. Synth. Catal. 2015; 357: 955
    • 24a Wu P, Wu K, Wang L, Yu Z. Org. Lett. 2017; 19: 5450
    • 24b Temperini A, Piazzolla F, Minuti L, Curini M, Siciliano C. J. Org. Chem. 2017; 82: 4588
    • 24c Grélaud S, Lusseau J, Massip S, Landais Y. Adv. Synth. Catal. 2017; 359: 2434
    • 24d Grélaud S, Desvergnes V, Landais Y. Org. Lett. 2016; 18: 1542
    • 24e Wu P, Wang L, Wu K, Yu Z. Org. Lett. 2015; 17: 868
    • 24f Zhu F, Wang Z.-X. Org. Lett. 2015; 17: 1601
    • 24g Stein AL, Bilheri FN, Zeni G. Chem. Commun. 2015; 51: 15522
    • 25a Elsherbini M, Hamama WS, Zoorob HH. Coord. Chem. Rev. 2017; 330: 110
    • 25b Perin G, Alves D, Jacob RG, Barcellos AM, Soares LK, Lenardão EJ. ChemistrySelect 2016; 2: 205
    • 25c Lenardão EJ, Soares LK, Barcellos AM, Perin G. Curr. Green Chem. 2016; 3: 4
    • 25d Santi C, Jacob RG, Monti B, Bagnoli L, Sancineto L, Lenardão EJ. Molecules 2016; 21: 1482
    • 25e Palomba M, Bagnoli L, Marini F, Santi C, Sancineto L. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 235
    • 25f Elsherbini M, Hamama WS, Zoorob HH. Coord. Chem. Rev. 2016; 312: 149
    • 25g Breder A, Ortigies S. Tetrahedron Lett. 2015; 56: 2843
    • 25h Santoro S, Azeredo JB, Nascimento V, Sancineto L, Braga AL, Santi C. RSC Adv. 2014; 4: 31521
    • 25i Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
    • 25j Perin G, Lenardão EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277
    • 26a Banerjee B, Koketsu M. Coord. Chem. Rev. 2017; 339: 104
    • 26b Rocha JB. T, Piccoli BC, Oliveira CS. ARKIVOC 2017; (ii): 457
    • 26c Barcellos AM, Abenante L, Sarro MT, Leo ID, Lenardão EJ, Perin G, Santi C. Curr. Org. Chem. 2017; 21: 2044
    • 26d Pacuła AJ, Mangiavacchi F, Sancineto L, Lenardão EJ, Ścianowski J, Santi C. Curr. Chem. Biol. 2015; 9: 97
    • 26e Orian L, Toppo S. Free Radical Biol. Med. 2014; 66: 65
    • 26f Santi C, Tidei C, Scalera C, Piroddi M, Galli F. Curr. Chem. Biol. 2013; 7: 25
    • 26g Fernandes AP, Gandin V. Biochim. Biophys. Acta, Gen. Subj. 2015; 1850, 1642
    • 26h Ninomiya M, Garud DR, Koketsu M. Coord. Chem. Rev. 2011; 255: 2968
    • 26i Nogueira CW, Rocha JB. T. Arch. Toxicol. 2011; 85: 1313
    • 26j Tinggi U. Environ. Health Prev. Med. 2008; 13: 102
    • 26k Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
    • 27a Liu H, Fang Y, Wang S.-Y, Ji S.-J. Org. Lett. 2018; 20: 930
    • 27b Thupyai A, Pimpasri C, Yotphan S. Org. Biomol. Chem. 2018; 16: 424
    • 27c Perin G, Roehrs JA, Hellwing PS, Stach G, Barcellos T, Lenardão EJ, Jacob RG, Luz EQ. ChemistrySelect 2017; 2: 4561
    • 27d Santos KS, Sandagorda EM. A, Cargnelutti R, Barcellos T, Jacob RG, Alves D, Schumacher RF. ChemistrySelect 2017; 2: 10793
    • 27e Lima DB, Penteado F, Vieira MM, Alves D, Perin G, Santi C, Lenardão EJ. Eur. J. Org. Chem. 2017; 3830
    • 27f Shi Q, Li P, Zhang Y, Wang L. Org. Chem. Front. 2017; 4: 1322
    • 27g Maity S, Karmakar U, Samanta R. Chem. Commun. 2017; 53: 12197
    • 27h Fang Y, Zhu Z.-L, Xu P, Wang S.-Y, Ji S.-J. Green Chem. 2017; 19: 1613
    • 27i Sun P, Jiang M, Wei W, Min Y, Zhang W, Li W, Yang D, Wang H. J. Org. Chem. 2017; 82: 2906
    • 27j Kibriya G, Samanta S, Singsardar M, Jana S, Hajra A. Eur. J. Org. Chem. 2017; 3055
    • 28a Cui F.-h, Chen J, Mo Z.-y, Su S.-x, Chen Y.-y, Ma X.-l, Tang H.-t, Wang H.-s, Pan Y.-m, Xu Y.-l. Org. Lett. 2018; 20: 925
    • 28b Padilha G, Birmann PT, Domingues M, Kaufman TS, Savegnago L, Silveira CC. Tetrahedron Lett. 2017; 58: 985
    • 28c Duarte LF. B, Barbosa ES, Oliveira RL, Pinz MP, Godoi B, Schumacher RF, Luchese C, Wilhelm EA, Alves D. Tetrahedron Lett. 2017; 58: 3319
    • 28d 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
    • 28e Kumar S, Sharma N, Maurya IK, Verma A, Kumar S, Bhasin KK, Sharma RK. New J. Chem. 2017; 41: 2919
    • 28f Zhang S, An B, Li J, Hu J, Huang L, Li X, Chan AS. C. Org. Biomol. Chem. 2017; 15: 7404
    • 29a Xu M, Zhang XH, Zhong P. Synth. Commun. 2012; 42: 3472
    • 29b Zora M, Demirci D, Kivrak A, Kelgokemen Y. Tetrahedron Lett. 2016; 57: 993
    • 29c Oliveira DH, Aquino TB, Nascimento JE. R, Perin G, Jacob RG, Alves D. Adv. Synth. Catal. 2015; 357: 4041
    • 30a Hati S, Dutta PK, Dutta S, Munshi P, Sen S. Org. Lett. 2016; 18: 3090
    • 30b Daswani U, Dubey N, Sharma P, Kumar A. New J. Chem. 2016; 40: 8093
    • 30c Chandra A, Parida KN, Moorthy JN. Tetrahedron 2017; 73: 5827
    • 30d Soldatova N, Postnikov P, Kukurina O, Zhdankin VV, Yoshimura A, Wirth T, Yusubov MS. ChemistryOpen 2017; 6: 18
    • 30e Olsen KL, Jensen MR, Mackay JA. Tetrahedron Lett. 2017; 58: 4111
    • 31a Uyanik M, Mutsuga T, Ishihara K. Angew. Chem. 2017; 129: 4014
    • 31b Bikshapathi R, Parvathaneni SP, Rao VJ. Green Chem. 2017; 19: 4446
    • 31c Zhao M, Lu W. Org. Lett. 2017; 19: 4560
    • 31d Shuler WG, Johnson SL, Hilinski MK. Org. Lett. 2017; 19: 4790
    • 31e Bikshapathi R, Prathima PS, Rao VJ. New J. Chem. 2016; 40: 10300
    • 31f Swamy T, Raviteja P, Srikanth G, Reddy BV. S, Ravinder V. Tetrahedron Lett. 2016; 57: 5596
    • 31g Soldatova N, Postnikov P, Troyan AA, Yoshimura A, Yusubov MS, Zhdankin VV. Tetrahedron Lett. 2016; 57: 4254
  • 32 Hussain H, Green IR, Ahmed I. Chem. Rev. 2013; 113: 3329
    • 33a Kupwade RV, Khot SS, Lad UP, Desai UV, Wadgaonkar PP. Res. Chem. Intermed. 2017; 43: 6875
    • 33b Sharma S, Pathare RS, Maurya AK, Gopal K, Roy TK, Sawant DM, Padasani RT. Org. Lett. 2016; 18: 356
    • 33c Parida KN, Chandra A, Moorthy JN. ChemistrySelect 2016; 3: 490
    • 33d Natarajan P. Tetrahedron Lett. 2015; 56: 4131
    • 33e Madabhushi S, Jillella R, Sriramoju V, Singh R. Green Chem. 2014; 16: 3125
    • 33f Wu G, Wu J, Wu J, Wu L. Synth. Commun. 2008; 38: 1036
    • 33g Khiar N, Mallouk S, Valdivia V, Bougrin K, Soufiaoui M, Fernández I. Org. Lett. 2007; 9: 1255
    • 33h Zolfigol MA, Niknam K, Bagherzadeh M, Ghorbani-Choghamarani A, Koukabi N, Hajjami M, Kolvari E. J. Chin. Chem. Soc. 2007; 54: 1115
    • 34a Ceccherelli P, Curini M, Epifano F, Marcotullio MC, Rosati O. J. Org. Chem. 1995; 60: 8412
    • 34b Palomba M, Trappetti F, Bagnoli L, Santi C, Marini F. Eur. J. Org. Chem. 2018; 3914
    • 34c Perin G, Santoni P, Barcellos AM, Nobre PC, Jacob RG, Lenardão EJ, Santi C. Eur. J. Org. Chem. 2018; 1224
    • 34d Perin G, Araujo DR, Nobre PC, Lenardão EJ, Jacob RG, Silva MS, Roehrs JA. PeerJ 2018; 6: e4706
    • 34e Rodrigues I, Barcellos AM, Belladona AL, Roehrs JA, Cargnelutti R, Alves D, Perin G, Schumacher RF. Tetrahedron 2018; 74: 4242
    • 34f Perin G, Duarte LF. B, Neto JS. S, Silva MS, Alves D. Synlett 2018; 29: 1479
    • 35a Perin G, Barcellos A, Luz EQ, Borges EL, Jacob RG, Lenardão EJ, Sancineto L, Santi C. Molecules 2017; 22: 327
    • 35b Thurow S, Penteado F, Perin G, Jacob RG, Alves D, Lenardão EJ. Green Chem. 2014; 16: 3854
  • 36 Zora M, Kivrak A, Yazici C. J. Org. Chem. 2011; 76: 6726
  • 37 Henriksen L, Stuhr-Hansen N. Phosphorus, Sulfur Silicon Relat. Elem. 1998; 136: 175
  • 38 Abdo M, Knapp S. J. Org. Chem. 2012; 77: 3433
  • 39 Sahoo H, Mandal A, Dana S, Baidya M. Adv. Synth. Catal. 2018; 360: 1099
  • 40 Tiecco M, Testaferri L, Tingoli M, Chianelli D, Bartoli D. Tetrahedron Lett. 1989; 30: 1417