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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Mini-Review Article

Selenocyclization by Formation of Carbon-nitrogen Bonds

Author(s): Biljana Šmit*, Petar B. Stanić and Nenad Janković*

Volume 19, Issue 3, 2022

Published on: 30 November, 2021

Page: [293 - 316] Pages: 24

DOI: 10.2174/1570179418666210917152537

Price: $65

Abstract

Selenium promoted-cyclization of unsaturated substrates containing internal nitrogen nucleophiles, such as different amines and amides, including the examples of its application in the synthesis of more complex polycyclic compounds is reviewed. Selenocyclization reactions of some more specific polyfunctional substrates, like Biginelli hybrids and hydantoins, are also covered.

Keywords: Selenium reagents, cyclization, cyclic amines, cyclic amides, lactamisation, fused rings.

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Graphical Abstract

[1]
Nicolaou, K.C.; Petasis, N.A. Selenium in Natural Products Synthesis; CIS: Philadelphia, 1984.
[2]
Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Oxford: Pergamon, 1986.
[3]
Liotta, D. Organoselenium Chemistry; Wiley: New York, 1987.
[4]
Patai, S. The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: New York, 1987.
[5]
Tiecco, M.; Tingoli, M.; Testaferri, L. The use of selenium containing intermediates to mediate or catalyze new organic reactions. Pure Appl. Chem., 1993, 65, 715-722.
[http://dx.doi.org/10.1351/pac199365040715]
[6]
Tiecco, M.; Testaferri, L.; Tingoli, M.; Bagnoli, L.; Marini, F.; Santi, C.; Temperini, A. Production and reactivity of new organoselenium intermediates 0 formation of carbon-oxygen and carbon-nitrogen bonds. Gazz. Chim. Ital., 1996, 126, 635-643.
[7]
Fujita, K. Recent advances in asymmetric oxyselenenylation and catalytic oxyselenenylation-deselenenylation. Rev. Heteroatom. Chem, 1997, 16(1997), 101-117.
[8]
Wessjohann, L.A.; Sinks, U. Benzeneselenenyl reagents in organic synthesis. J. Prakt. Chem., 1998, 340, 189-203.
[http://dx.doi.org/10.1002/prac.19983400302]
[9]
Tiecco, M. Organoselenium Chemistry: Modern developments in organic synthesis. In: Topics in Current Chemistry; Wirth, T, Ed.; Springer-Verlag: Heideberg,, 2000; Vol. 208, pp. 7-54.
[10]
Back, T.G., Ed.; Organoselenium Chemistry: A Practical Approach; Oxford University Press: Oxford, 1999.
[11]
Santi, C.; Santoro, S. Organoselenium chemistry: synthesis and reactions; Wirth, T, Ed.; Wiley-VCH: Wenheim, 2012, pp. 1-51.
[12]
Wirth, T. Organoselenium chemistry in stereoselective reactions. Angew. Chem. Int. Ed. Engl., 2000, 39(21), 3740-3749.
[http://dx.doi.org/10.1002/1521-3773(20001103)39:21<3740::AIDANIE3740>3.0.CO;2-N] [PMID: 11091451]
[13]
Petragnani, N.; Stefani, H.A.; Valduga, C.J. Recent advances in selenocyclofunctionalization reactions. Tetrahedron, 2001, 57, 1411.
[http://dx.doi.org/10.1016/S0040-4020(00)01033-4]
[14]
Tiecco, M.; Testaferri, L.; Bagnoli, L.; Marini, F.; Santi, C.; Temperini, A.; Scarponi, C.; Sternativo, S.; Terlizzi, R.; Tomassini, C. Enantioselective synthesis of heterocyclic compounds mediated by organoselenium reagents. ARKIVOC, 2006, (vii), 186.
[http://dx.doi.org/10.3998/ark.5550190.0007.715]
[15]
Soloshonok, V.A.; Nelson, D.J. Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation. Beilstein J. Org. Chem., 2011, 7, 744-758.
[http://dx.doi.org/10.3762/bjoc.7.85] [PMID: 21804870]
[16]
Lenardão, E.J.; Santi, C.; Sancineto, L. New Frontiers in Organoselenium Compounds; Springer International Publishing, 2018.
[http://dx.doi.org/10.1007/978-3-319-92405-2_2]
[17]
Jain, V.K.; Priyadarsini, K.I., Eds.; Organoselenium Compounds in Biology and Medicine: Synthesis, Biological and Therapeutic Treatments; Royal Society of Chemistry, 2018.
[18]
Nogueira, C.W.; Zeni, G.; Rocha, J.B.T. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem. Rev., 2004, 104(12), 6255-6285.
[http://dx.doi.org/10.1021/cr0406559] [PMID: 15584701]
[19]
Fernandes, A.P.; Gandin, V. Selenium compounds as therapeutic agents in cancer. Biochim. Biophys. Acta, 2015, 1850(8), 1642-1660.
[http://dx.doi.org/10.1016/j.bbagen.2014.10.008] [PMID: 25459512]
[20]
Pacula, A.J.; Mangiavacchi, F.; Sancineto, L.; Lenardao, E.J.; Scianowski, J.; Santi, C. An update on “Selenium containing compounds from poison to drug candidates: A review on the GPx-like activity”. Curr. Chem. Biol., 2015, 9, 97-112.
[http://dx.doi.org/10.2174/2212796810666160120220725]
[21]
Reich, H.J.; Hondal, R.J. Why nature chose selenium. ACS Chem. Biol., 2016, 11(4), 821-841.
[http://dx.doi.org/10.1021/acschembio.6b00031] [PMID: 26949981]
[22]
Barbosa, N.V.; Nogueira, C.W.; Nogara, P.A.; de Bem, A.F.; Aschner, M.; Rocha, J.B.T. Organoselenium compounds as mimics of selenoproteins and thiol modifier agents. Metallomics, 2017, 9(12), 1703-1734.
[http://dx.doi.org/10.1039/C7MT00083A] [PMID: 29168872]
[23]
Tiecco, M. Electrophilic Selenium, Selenocyclizations. In: Topics in Current Chemistry; Thomas, Wirth, Ed.; Springer: Berlin, Heidelberg, 2000; Vol. 208, pp. 7-54.
[24]
Palomba, M.; Mangiavacchi, F.; Marini, F. Recent advances in selenium promoted or catalyzed electrophilic aminations of alkenes and alkynes. ARKIVOC, 2019, 2, 114-143.
[http://dx.doi.org/10.24820/ark.5550190.p011.075]
[25]
Shao, L.; Li, Y.; Lu, J.; Jiang, X. Recent progress in selenium-catalyzed organic reactions. Org. Chem. Front., 2019, 6, 2999-3041.
[http://dx.doi.org/10.1039/C9QO00620F]
[26]
Mojsilović, B.M.; Bugarčić, Z.M. Pyridine-facilitated phenylselenoetherification of some tertiary alkenols. Heteroatom Chem., 2001, 12, 454-479.
[http://dx.doi.org/10.1002/hc.1072]
[27]
Bugarčić, Z.M.; Dunkić, J.D.; Mojsilović, B.M. A simple, convenient and expeditious approach to cineol. Heteroatom Chem., 2004, 15, 468-470.
[http://dx.doi.org/10.1002/hc.20044]
[28]
Bugarčić, Z.M.; Mojsilović, B.M. An improved procedure for phenylselenoetherification of some Δ5-alkenols using pyridine, Ag2O, and some Lewis acids as catalysts. Heteroatom Chem., 2004, 15, 146-149.
[http://dx.doi.org/10.1002/hc.10227]
[29]
Bugarčić, Z.M.; Mojsilović, B.M.; Divac, V.M. Facile pyridine-catalyzed phenylselenoetherification of alkenols. J. Mol. Catal. Chem., 2007, 272, 288-292.
[http://dx.doi.org/10.1016/j.molcata.2007.03.058]
[30]
Šmit, B.; Bugarčić, Z. Phenylselenoetherification of some Δ4-alkenols facilitated by pyridine and some Lewis acids. J. Heterocycl. Chem., 2010, 47, 1443-1446.
[http://dx.doi.org/10.1002/jhet.487]
[31]
Berthe, B.; Outurquin, F.; Paulmier, C. Synthesis of azetidines by electrophilic selenium-induced cyclization of homoallylic benzylamines. Tetrahedron Lett., 1997, 38, 1393-1396.
[http://dx.doi.org/10.1016/S0040-4039(97)00028-2]
[32]
Nicolaou, K.C.; Roecker, A.J.; Hughes, R.; van Summeren, R.; Pfefferkorn, J.A.; Winssinger, N. Novel strategies for the solid phase synthesis of substituted indolines and indoles. Bioorg. Med. Chem., 2003, 11(3), 465-476.
[http://dx.doi.org/10.1016/S0968-0896(02)00386-3] [PMID: 12517442]
[33]
Franck, X.; Leleu, S.; Outurquin, F. Regioselective synthesis of azetidines of pyrrolidines by selenium-induced cyclization of secoundary homoallylic amines. Tetrahedron Lett., 2010, 51, 4437-4440.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.087]
[34]
Okuma, K.; Seto, J-I. Synthesis of indoles,3,1-benzoxazines, and quinolines from 2-alkenylanilides and active seleniums. Phosphorus Sulfur Silicon Relat. Elem., 2010, 185, 1014-1020.
[http://dx.doi.org/10.1080/10426501003772169]
[35]
Tang, E.; Chen, B.; Zhang, L.; Li, W.; Lin, J. ZnCl2-catalyzed intramolecular cyclization of 2-aminochalcones using polymer-supported selenium reagent: synthesis of 2-phenyl-4-quinolones and 2-phenyl-2,3-dihydroquinolin-4(1H)-one. Synlett, 2011, 5, 707-711.
[http://dx.doi.org/10.1055/s-0030-1259549]
[36]
Tiecco, M. Farmacy Faculty, University of Perugia.
[37]
Wilson, S.R.; Sawicki, R.A. Transannular cyclizations of 1-aza-4-cyclooctene. J. Org. Chem., 1979, 44, 287-291.
[http://dx.doi.org/10.1021/jo01316a027]
[38]
Clive, D.L.J.; Wong, C.K.; Kiel, W.W.; Menchen, S.M. Cyclofunctionalisation of olefinic urethanes with benzeneseleneyl reagents: a new general synthesis of nitrogen heterocycles. J. Chem. Soc. Chem. Commun., 1978, 9, 379-380.
[http://dx.doi.org/10.1039/c39780000379]
[39]
Clive, D.L.J.; Farina, V.; Singh, A.; Wong, C.K.; Kiel, W.A.; Menchen, S.M. Cyclofunctionalization of olefinic urethanes using benzeneselenenyl chloride in the presence of silica gel: A general route to nitrogen heterocycles. J. Org. Chem., 1980, 45, 2120-2126.
[http://dx.doi.org/10.1021/jo01299a019]
[40]
Toshimitsu, A.; Terao, K.; Uemura, S. Intramolecular amidoselenation of N-alkenyl amides: formation of nitrogen heterocycles. J. Org. Chem., 1986, 51, 1724-1729.
[http://dx.doi.org/10.1021/jo00360a017]
[41]
Webb, R.; Danishefsky, S. Ureidoallylation of double bonds. Tetrahedron Lett., 1983, 24, 1357-1360.
[http://dx.doi.org/10.1016/S0040-4039(00)81655-X]
[42]
Izumi, T.; Sugano, M.; Konno, T. Synthesis of indoles via amidoselenation. J. Heterocycl. Chem., 1992, 29, 899-904.
[http://dx.doi.org/10.1002/jhet.5570290437]
[43]
Ninoi, T.; Hasegawa, Y.; Yoshihara, M.; Maeshina, T.; Fujii, M.; Aida, T. Asymmetric electrophilic cyclization of N-(4-pentenyl) amides. Chem. Express, 1989, 4, 709-712.
[44]
Francisco, C.G.; Hernandez, R.; Leon, E.I.; Salazar, J.A.; Suarez, E. Aminoselenenylation of alkenes: syntheses of β-phenylseleno carbamates and β-phenylseleno cyanamides. J. Chem. Soc., Perkin Trans. 1, 1990, 2417-2427.
[http://dx.doi.org/10.1039/P19900002417]
[45]
Cooper, M.; Ward, D. Selenium induced stereoselective cyclization of N-protected 3-hydroxy-4-pentenylamines. Tetrahedron Lett., 1992, 33, 5999-6002.
[http://dx.doi.org/10.1016/S0040-4039(00)61110-3]
[46]
Cooper, M.A.; Ward, A.D. Cyclizations using selenium chemistry for substituted 3-hydroxypiperidines and 3-hydroxypyrrolidines. Aust. J. Chem., 2011, 64, 1327-1338.
[http://dx.doi.org/10.1071/CH11073]
[47]
Cooper, M.; Ward, D. Selenium induced stereoselective cyclization of N-substituted-4-hydroxy-5-hexenylamines. Tetrahedron Lett., 1994, 35, 5065-5068.
[http://dx.doi.org/10.1016/S0040-4039(00)73321-1]
[48]
Tiecco, M.; Tetafferi, L.; Bagnoli, L.; Scarponi, C.; Temperini, A.; Marini, F.; Santi, C. Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols. Tetrahedron Asymmetry, 2007, 18, 2758-2767.
[http://dx.doi.org/10.1016/j.tetasy.2007.11.003]
[49]
Chen, F.; Tan, C.K.; Yeung, Y-Y. C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization. J. Am. Chem. Soc., 2013, 135(4), 1232-1235.
[http://dx.doi.org/10.1021/ja311202e] [PMID: 23312005]
[50]
Guo, R.; Huang, J.; Huang, H.; Zhao, X. Organoselenium-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles. Org. Lett., 2016, 18(3), 504-507.
[http://dx.doi.org/10.1021/acs.orglett.5b03543] [PMID: 26794425]
[51]
Horibe, T.; Ohmura, S.; Ishihara, K. Selenium-iodine cooperative catalyst for chlorocyclofunctionalization of tryptamine derivatives. Org. Lett., 2017, 19(20), 5525-5528.
[http://dx.doi.org/10.1021/acs.orglett.7b02613] [PMID: 28956932]
[52]
Lim, H.J. RajanBabu, T.V. Seleniranium ion-triggered reactions: new aspects of Friedel-Crafts and N-detosylative cyclizations. Org. Lett., 2009, 11(13), 2924-2927.
[http://dx.doi.org/10.1021/ol900961m] [PMID: 19507847]
[53]
Conner, E.S.; Crocker, K.E.; Fernando, R.G.; Fronczek, F.R.; Stanley, G.G.; Ragains, J.R. Visible-light-promoted selenofunctionalization of alkenes. Org. Lett., 2013, 15(21), 5558-5561.
[http://dx.doi.org/10.1021/ol402753u] [PMID: 24134120]
[54]
Zhang, Q-B.; Yuan, P-F.; Kai, L-L.; Liu, K.; Ban, Y-L.; Wang, X-Y.; Wu, L-Z.; Liu, Q. Heterocycles via visible-light-driven aerobic selenation of olefins with diselenides. Org. Lett., 2019, 21(4), 885-889.
[http://dx.doi.org/10.1021/acs.orglett.8b03738] [PMID: 30698980]
[55]
De Kimpe, N.; Boelens, M. Organoselenium-induced cyclization of γ,δ-alkenimines to nitrogen heterocycles. J. Chem. Soc. Chem. Commun., 1993, 9, 916-918.
[http://dx.doi.org/10.1039/C39930000916]
[56]
De Smaele, D.; De Kimpe, N. Synthesis of functionalized pyrrolidines from N-(benzylidiene)- and N-(alkylidiene)-homoallylamines. J. Chem. Soc. Chem. Commun., 1995, 19, 2029-2030.
[http://dx.doi.org/10.1039/c39950002029]
[57]
Toshimitsu, A.; Terao, K.; Uemura, S. Intramolecular amidoselenilation of N-alkenyl imidates to N-heterocycles. J. Chem. Perkin Trans., 1986, 1, 1837-1843.
[58]
Tiecco, M.; Testafferi, L.; Tingoli, M.; Santi, C. New synthesis of isoxazolidines from the selenium-induced cyclization of O-Allyl Hydroxylamines. Tetrahedron Lett., 1995, 36, 163-166.
[http://dx.doi.org/10.1016/0040-4039(94)02201-L]
[59]
Tiecco, M.; Testafferi, L.; Tingoli, M.; Bagnoli, L. Organoselenium-induced stereoselective cyclisation of O-allyl oximes: a new synthetic route to isoxazolidines. J. Chem. Soc. Chem. Commun., 1995, 235-236.
[http://dx.doi.org/10.1039/c39950000235]
[60]
Tiecco, M.; Testafferi, L.; Tingoli, M.; Bagnoli, L.; Santi, C. Selenium-induced cyclization of O-allyl oximes as a synthetic route to N-alkyl isoxazolidines. Tetrahedron, 1995, 51, 1277-1284.
[http://dx.doi.org/10.1016/0040-4020(94)01006-L]
[61]
Tiecco, M.; Testafferi, L.; Marini, F.; Sternativo, S.; Bagnoli, L.; Santi, C.; Temperini, A. Optically active isoxazolidines and 1,3-amino alcohols by asymmetric selenocyclization reactions of O-allyl oximes. Tetrahedron Asymmetry, 2001, 12, 3053-3059.
[http://dx.doi.org/10.1016/S0957-4166(01)00543-2]
[62]
Tiecco, M.; Testafferi, L.; Tingoli, M.; Bagnoli, L.; Marini, F. Ring-closure reactions of alkenyl oximes induced by persulfate anion oxidation of diphenyl diselenide. Formation of 1,2-oxazines and cyclic nitrones. J. Chem. Soc., Perkin Trans. 1, 1993, 1989-1993.
[http://dx.doi.org/10.1039/p19930001989]
[63]
Tiecco, M.; Testaferri, L.; Bagnoli, L.; Purgatorio, V.; Temperini, A.; Marini, F.; Santi, C. Efficient asymmetric selenocyclizations of alkenyl oximes into cyclic nitrones and 1,2-oxazines promoted by sulfur containing diselenides. Tetrahedron Asymmetry, 2001, 12, 3297-3304.
[http://dx.doi.org/10.1016/S0957-4166(02)00013-7]
[64]
Tiecco, M.; Testafferi, L.; Marini, F.; Bagnoli, L.; Santi, C.; Temperini, A. Phenylselenenyl sulfate induced cyclization of allylhydrazines. Synthesis of pyrazole derivatives. Tetrahedron, 1997, 53, 4441-4446.
[http://dx.doi.org/10.1016/S0040-4020(97)00116-6]
[65]
Tiecco, M.; Testafferi, L.; Marini, F. Factors controlling the selenium-induced cyclizations of alkenyl hydrazines to pyridazine or pyrrolidinamine derivatives. Tetrahedron, 1997, 53, 10591-10602.
[http://dx.doi.org/10.1016/S0040-4020(97)00670-4]
[66]
Tiecco, M.; Testafferi, L.; Marini, F.; Santi, C.; Bagnoli, L.; Temperini, A. Pyrrolidinamine, piperidinamine and tetrahydropyridazine derivatives from selenium promoted cyclization of alkenyl phenylhydrazones. Tetrahedron, 1997, 53, 7311-7318.
[http://dx.doi.org/10.1016/S0040-4020(97)00414-6]
[67]
Toshimitsu, A.; Terao, K.; Uemura, S. Intramolecular amidoselenation leading to lactams by the reaction of N-alkylalkenylamides with benzenselenenyl chloride. Tetrahedron Lett., 1984, 25, 5917-5920.
[http://dx.doi.org/10.1016/S0040-4039(01)81720-2]
[68]
Toshimitsu, A.; Terao, K.; Uemura, S. Intramolecular amidoselenation of olefinic imidates to afford lactams. J. Chem. Soc. Chem. Commun., 1986, 530-531.
[http://dx.doi.org/10.1039/c39860000530]
[69]
Wang, X-Y.; Zhong, Y-F.; Mo, Z-Y.; Wu, S-H.; Xu, Y-L.; Tang, H-T.; Pan, Y-M. Synthesis of seleno oxindles via electrochemical cyclization of N-acrylamides with diorganyl diselenides. Adv. Synth. Catal., 2021, 363, 208-214.
[http://dx.doi.org/10.1002/adsc.202001192]
[70]
Fu, W-J.; Zhu, M.; Zou, G-L. Synthesis of 3,3-disubstituted seleno oxindoles by organoselenium-induced radical cyclizations of N-arylacrylamides. Heterocycl. Commun., 2015, 21, 9-12.
[http://dx.doi.org/10.1515/hc-2014-0195]
[71]
Chung, S.K.; Jeong, T.H.; Kang, D.H. A diastereoselective phenylselenium-induced lactamization of olefinic amides. A possible route to α-and β-amino acid derivatives. Tetrahedron Asymmetry, 1997, 8, 5-9.
[http://dx.doi.org/10.1016/S0957-4166(96)00496-X]
[72]
Chung, S.K.; Jeong, T.H.; Kang, D.H. Novel asymmetric phenylselenium-induced lactamizations of olefinic amides: stereoselective routes to α- and β-amino acids. J. Chem. Soc., Perkin Trans. 1, 1998, 969-976.
[http://dx.doi.org/10.1039/a705390h]
[73]
Zhang, Y.; Shao, Y.; Gong, J.; Zhu, J.; Cheng, T.; Chen, J. Selenium-catalyzed oxidative C0H amination of (E)-3-(arylamino)-2-styrylquinazolin-4(3H)-ones: A metal-free synthesis of 1,2-diarylpyrazolo[5,1-b]quinazolin-9(1H)-ones. J. Org. Chem., 2019, 84(5), 2798-2807.
[http://dx.doi.org/10.1021/acs.joc.8b03179] [PMID: 30740976]
[74]
Edstrom, E.D. New methodology for the synthesis of functionalized indolizidine and quinolizidine ring systems. J. Am. Chem. Soc., 1991, 113, 6690-6692.
[http://dx.doi.org/10.1021/ja00017a060]
[75]
Edstrom, E.D. An unexpected reversal in the stereochemistry of transannular cyclizations. A stereoselective synthesis of (±)-epilupinine. Tetrahedron Lett., 1991, 32, 5709-5712.
[http://dx.doi.org/10.1016/S0040-4039(00)93536-6]
[76]
Diederich, M.; Nubbemeyer, U. Diastereoselective zwitterionic aza‐Claisen rearrangement: Synthesis of nine‐membered ring lactams and transannular ring contraction. Chemistry, 1996, 2, 894.
[http://dx.doi.org/10.1002/chem.19960020721]
[77]
Sudau, A.; Nubbemeyer, U. Unusual diastereoselection in the synthesis of nine‐membered ring lactams and conformation‐controlled transannular reactions to generate optically active indolizidinones. Angew. Chem. Int. Ed. Engl., 1998, 37(8), 1140-1143.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1140:AID-ANIE1140>3.0.CO;2-W] [PMID: 29711014]
[78]
Šmit, B.; Pavlović, R.Z. Three-step synthetic pathway to fused bicyclic hydantoins involving a selenocyclization step. Tetrahedron, 2015, 71, 1101-1108.
[http://dx.doi.org/10.1016/j.tet.2014.12.088]
[79]
Šmit, B.M.; Pavlović, R.Z.; Milenković, D.A.; Marković, Z.S. Mechanism, kinetics and selectivity of selenocyclization of 5-alkenylhydantoins: an experimental and computational study. Beilstein J. Org. Chem., 2015, 11, 1865-1875.
[http://dx.doi.org/10.3762/bjoc.11.200] [PMID: 26664604]
[80]
Šmit, B.; Rodić, M.; Pavlović, R.Z. Synthesis of angularly fused (homo)triquinane type hydantoins as precursors of bicyclic α-prolines. Synthesis, 2016, 48, 387-393.
[http://dx.doi.org/10.1055/s-0035-1561285]
[81]
Šmit, B.; Stanić, P.B.; Joksović, Lj.G.; Ašanin, D.P.; Simić, Z. Influence of electrochemical conditions on the regio- and stereoselectivity of selenocyclization of alkenyl hydantoins. J. Serb. Chem. Soc., 2021, 86, 585-590.
[http://dx.doi.org/10.2298/JSC201022023S]
[82]
Janković, N. 2019.
[83]
Toshimitsu, A.; Terao, K.; Uemura, S. Organoselenium-induced cyclization of olefinic imidates and amides. Selective synthesis of lactams or iminolactones. J. Org. Chem., 1987, 52, 2018-2026.
[http://dx.doi.org/10.1021/jo00386a022]
[84]
Tiecco, M.; Testafferi, L.; Tingoli, M.; Marini, F. N-hydroxy γ-lactams or cyclic N-hydroxy imidates from the organoselenium-induced cyclization of β,γ-unsaturated hydroxamic acids. J. Chem. Soc. Chem. Commun., 1994, 221-222.
[http://dx.doi.org/10.1039/C39940000221]
[85]
Tiecco, M.; Testafferi, L.; Marini, F.; Sternativo, S.; Bagnoli, L.; Santi, C.; Temperini, A. A sulfur-containing diselenide as an efficient chiral reagent in asymmetric selenocyclization reactions. Tetrahedron Asymmetry, 2001, 12, 1493-1502.
[http://dx.doi.org/10.1016/S0957-4166(01)00248-8]
[86]
Li, X.; He, P.; Zhou, H-B.; Dong, C. One-step pathway to selenoisobenzofuran-1(3H)-imine derivatives through highly selective selenocyclization of olefinic amides with benzeneselenyl chloride. Org. Biomol. Chem., 2018, 16(12), 2150-2155.
[http://dx.doi.org/10.1039/C8OB00179K] [PMID: 29517094]
[87]
Wirth, T.; Fragale, G. Stereoselective isoquinoline alkaloid synthesis with new diselenides. Synthesis, 1998, 162-166.
[http://dx.doi.org/10.1055/s-1998-2011]
[88]
Marsden, S.P.; Depew, K.M.; Danishefsky, S.J. Stereoselective total syntheses of amauromine and 5-N-acetylardeemin. A concise route to the family of “reverse-prenylated” hexahydropyrroloindole alkaloids. J. Am. Chem. Soc., 1994, 116, 11143-11144.
[http://dx.doi.org/10.1021/ja00103a034]
[89]
Ley, S.V.; Cleator, E.; Hewitt, P.R. A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones. Org. Biomol. Chem., 2003, 1(20), 3492-3494.
[http://dx.doi.org/10.1039/B308288A] [PMID: 14599007]
[90]
Oelke, A.J.; France, D.J.; Hofmann, T.; Wuitschik, G.; Ley, S.V. Total synthesis of chloptosin. Angew. Chem. Int. Ed. Engl., 2010, 49(35), 6139-6142.
[http://dx.doi.org/10.1002/anie.201002880] [PMID: 20645377]
[91]
Yu, S-M.; Hong, W-X.; Wu, Y.; Zhong, C-L.; Yao, Z-J. Total synthesis of chloptosin, a potent apoptosis-inducing cyclopeptide. Org. Lett., 2010, 12(5), 1124-1127.
[http://dx.doi.org/10.1021/ol100135a] [PMID: 20136143]
[92]
Hewitt, P.R.; Cleator, E.; Ley, S.V. A concise total synthesis of (+)-okaramine C. Org. Biomol. Chem., 2004, 2(17), 2415-2417.
[http://dx.doi.org/10.1039/b410180d] [PMID: 15326519]
[93]
Shibahara, S.; Matsubara, T.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Total synthesis of NW-G01, a cyclic hexapeptide antibiotic, and 34-epi-NW-G01. Org. Lett., 2011, 13(17), 4700-4703.
[http://dx.doi.org/10.1021/ol201912w] [PMID: 21809853]
[94]
Depew, K.M. Marsden, S.P.; Zatorska, D.; Zatorski, A.; Bornmann, W.G.; Danishefsky, S.J. Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes potential MDR reversal agents. J. Am. Chem. Soc., 1999, 121, 11953-11963.
[http://dx.doi.org/10.1021/ja991558d]
[95]
Wei, Q.; Wang, Y-Y.; Du, Y-L.; Gong, L.Z. Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives. Beilstein J. Org. Chem., 2013, 9, 1559-1564.
[http://dx.doi.org/10.3762/bjoc.9.177] [PMID: 23946855]
[96]
Horibe, T.; Ohmura, S.; Ishihara, K. Selenium-iodine cooperative catalyst for chlorocyclization of tryptamine derivatives. Org. Lett., 2017, 19(20), 5525-5528.
[http://dx.doi.org/10.1021/acs.orglett.7b02613] [PMID: 28956932]

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