Synthesis, Table of Contents Synthesis 2024; 56(01): 171-178DOI: 10.1055/a-2175-1008 paper Synthesis of Oxindoles via SmI2-Promoted Reduction of 2-Nitrophenylacetic Acids Authors Pengkai Wang Songlin Zhang∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract The reduction of 2-nitrophenylacetic acids to oxindoles promoted by SmI2 is reported for the first time. This reaction involving the reduction of nitro group proceeds through N–O bond cleavage and direct condensation with the neighboring carboxyl group. From a synthetic point of view, a new method for the synthesis of oxindoles in mild neutral conditions is developed. Key words Key wordssamarium diiodide - single electron transfer reagent - oxindoles Full Text References References 1a Goehring RR, Sachdeva YP, Pisipati JS, Sleevi MC, Wolfe JF. J. Am. Chem. Soc. 1985; 107: 435 1b Higuchi K, Kawasaki T. Nat. Prod. Rep. 2007; 24: 843 1c Naresh Babu K, Kariyandi NR, Saheeda MK. S, Kinthada LK, Bisai A. J. Org. Chem. 2018; 83: 12664 1d Barja I, Piñeiro A, Ruiz-González A, Caro A, López P, Martín J. Sci. Rep. 2023; 13: 6669 1e Singh J, Sharma A. Adv. Synth. Catal. 2021; 363: 4284 1f Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748 1g Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Cremonini MA, Placucci G, Cervellati R, Greco E. Eur. J. Med. Chem. 2010; 45: 1374 2a Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Cremonini MA, Placucci G, Cervellati R, Greco E. Eur. J. Med. Chem. 2010; 45: 1374 2b Roth GJ, Heckel A, Colbatzky F, Handschuh S, Kley J, Lehmann-Lintz T, Lotz R, Tontsch-Grunt U, Walter R, Hilberg F. J. Med. Chem. 2009; 52: 4466 2c van Deurzen MP. J, van Rantwijk F, Sheldon RA. J. Mol. Catal. B: Enzym. 1996; 2: 33 2d Yong SR, Ung AT, Pyne SG, Skelton BW, White AH. Tetrahedron 2007; 63: 5579 2e Watanabe H, Ono M, Kimura H, Matsumura K, Yoshimura M, Okamoto Y, Ihara M, Takahashi R, Saji H. Bioorg. Med. Chem. Lett. 2012; 22: 5700 2f Singh H, Sindhu J, Khurana JM, Sharma C, Aneja KR. Eur. J. Med. Chem. 2014; 77: 145 3 Hoessel R, Leclerc S, Endicott JA, Nobel ME. M, Lawrie A, Tunnah P, Leost M, Damiens E, Marie D, Marko D, Niederberger E, Tang W, Eisenbrand G, Meijer L. Nat. Cell. Biol. 1999; 1: 60 4 Murphy JA, Tripoli R, Khan TA, Mali UW. Org. Lett. 2005; 7: 3287 5 Wyle G, Appelboom T, Bolten W, Breedveld FC, Feely J, Leeming MR. G, Le Loet X, Manthorpe R, Marcolongo R, Smolen J. Rheumatology 1995; 34: 554 6 Ansar SA, Aggarwal S, Arya S, Haq MA, Mittal V, Gared F. Sci. Rep. 2023; 13: 7051 7 Greenberg WM, Citrome L. CNS Drug Rev. 2007; 13: 137 8 Kaur M, Singh M, Chadha N, Silakari O. Eur. J. Med. Chem. 2016; 123: 858 9 Crestini C, Saladino R. Synth. Commun. 1994; 24: 2835 10a Wu L, Falivene L, Drinkel E, Grant S, Linden A, Cavallo L, Dorta R. Angew. Chem. Int. Ed. 2012; 51: 2870 10b Shaughnessy KH, Hamann BC, Hartwig JF. J. Org. Chem. 1998; 63: 6546 10c Spallek MJ, Riedel D, Rominger F, Hashmi AS. K, Trapp O. Organometallics 2012; 31: 1127 11a Ju X, Liang Y, Jia P, Li W, Yu W. Org. Biomol. Chem. 2012; 10: 498 11b Cabri W, Candiani I, Colombo M, Franzoi L, Bedeschi A. Tetrahedron Lett. 1995; 36: 949 12a RajanBabu TV, Chenard BL. J. Org. Chem. 1986; 51: 1704 12b Cortese NA, Heck RF. J. Org. Chem. 1977; 42: 3491 12c Sestito S, Nesi G, Daniele S, Martelli A, Digiacomo M, Borghini A, Pietra D, Calderone V, Lapucci A, Falasca M, Parrella P, Notarangelo A, Breschi MC, Macchia M, Martini C, Rapposelli S. Eur. J. Med. Chem. 2015; 105: 274 12d Lin N, Xia P, Kovar P, Park C, Chen Z, Zhang H, Rosenberg SH, Sham HL. Bioorg. Med. Chem. Lett. 2006; 16: 421 13 Girard P, Namy JL, Kagan HB. J. Am. Chem. Soc. 1980; 102: 2693 14a Gopalaiah K, Kagan HB. Chem. Rec. 2013; 13: 187 14b Procter DJ, Flowers RA, Skrydstrup T. Organic Synthesis Using Samarium Diiodide: A Practical Guide . The Royal Society of Chemistry; Cambridge: 2009 14c Hu Y.-J, Gu C.-C, Wang X.-F, Min L, Li C.-C. J. Am. Chem. Soc. 2021; 143: 17862 14d Shi SC, Szostak M. Molercules 2017; 22: 2018 14e Ishida T, Takemoto Y. Tetrahedron 2013; 69: 4517 14f Just-Baringo X, Procter DJ. Acc. Chem. Res. 2015; 48: 1263 15a Souppe J, Danon L, Namy JL, Kagan HB. J. Organomet. Chem. 1983; 250: 227 15b Zhang Y, Lin R. Synth. Commun. 1987; 17: 329 15c Kende AS, Mendoza JS. Tetrahedron Lett. 1991; 32: 1699 15d Brady ED, Clark DL, Keogh DW, Scott BL, Watkin JG. J. Am. Chem. Soc. 2002; 124: 7007 15e Ferreira Ramos JA, Araújo CS, Nagem TJ, Taylor JG. J. Heterocycl. Chem. 2015; 52: 54 16a Kamochi Y, Kudo T. Tetrahedron Lett. 1991; 32: 3511 16b Kamochi Y, Kudo T. Chem. Lett. 1993; 22: 1495 17a Mukaiyama T, Yorozu K, Kato K, Yamada T. Chem. Lett. 1992; 21: 181 17b Huang F, Zhang SL. Org. Lett. 2019; 21: 7430 17c Ning L, Li HZ, Lai ZM, Szostak M, Chen XY, Dong YH, Jin SH, An J. J. Org. Chem. 2021; 86: 2907 18 Surasani SR, Maity S. ChemistrySelect 2017; 2: 598 19 Albaugh P, Fan Y, Mi Y, Sun F, Adrian F, Li N, Jia Y, Sarkisova Y, Kreusch A. ACS Med. Chem. Lett. 2012; 3: 140 20 Conde JJ, McGuire M, Wallace M. Tetrahedron Lett. 2003; 44: 3081 21 Kotzur N, Briand B, Beyermann M, Hagen V. J. Am. Chem. Soc. 2009; 131: 16927 22 Achmatowicz M, Thiel OR, Gorins G, Goldstein C, Affouard C, Jensen R, Larsen RD. J. Org. Chem. 2008; 73: 6793 23 Bernard-Gauthier V, Aliaga A, Aliaga A, Boudjemeline M, Hopewell R, Kostikov A, Rosa-Neto P, Thiel A, Schirrmacher R. ACS Chem. Neurosci. 2015; 6: 260 24 Liu H, Zhou S, Wen G, Liu X, Liu D, Zhang Q, Schmidt RR, Sun J. Org. Lett. 2019; 21: 8049 25 Parkes KE. B, Ermert P, Fässler J, Ives J, Martin JA, Merrett JH, Obrecht D, Williams G, Klumpp K. J. Med. Chem. 2003; 46: 1153 26 Lu G, Huang T, Hsueh H, Yang S, Cho T, Chou H. Chem. Commun. 2021; 57: 4839 27 Liu L, Li Y, Wang F, Ning R, Kong D, Wu M. ARKIVOC 2022; (v): 135 28 Gandeepan P, Rajamalli P, Cheng CH. Synthesis 2016; 48: 1872 29 Aslan M, Taskesenligil Y, Pıravadılı S, Saracoglu N. J. Org. Chem. 2022; 87: 5037 30 Chen JJ, Wei Y, Drach JC, Townsend LB. J. Med. Chem. 2000; 43: 2449 31 Zhao G, Liang L, Wang E, Lou S, Qi R, Tong R. Green Chem. 2021; 23: 2300 32 Beckett AH, Daisley RW, Walker J. Tetrahedron 1968; 24: 6093 33 Tian X, Li X, Duan S, Du Y, Liu T, Fang Y, Chen W, Zhang H, Li M, Yang X. Adv. Synth. Catal. 2021; 363: 1050 34 Doğan SD, Demirpolat E, Yerer Aycan MB, Balci M. Tetrahedron 2015; 71: 252 35 Lu G, Huang T, Hsueh H, Yang S, Cho T, Chou H. Chem. Commun. 2021; 57: 4839 36 Heyder L, Hochban PM. M, Taylor C, Chevillard F, Siefker C, Iking C, Borchardt H, Aigner A, Klebe G, Heine A, Kolb P, Diederich WE. Eur. J. Med. Chem. 2023; 245: 114914 37 Keum H, Jung H, Jeong J, Kim D, Chang S. Angew. Chem. Int. Ed. 2021; 60: 25235 38 Álvarez-Constantino AM, Álvarez-Pérez A, Varela JA, Sciortino G, Ujaque G, Saá C. J. Org. Chem. 2023; 88: 1185 Supplementary Material Supplementary Material Supporting Information (PDF)
