Bagley, M. et al.: 2018 Science of Synthesis: Knowledge Updates 2018/3 DOI: 10.1055/sos-SD-115-00563
Knowledge Updates 2018/3

15.6.3 Isoquinolinones (Update 2018)

More Information

Book

Editors: Bagley, M.; Banert, K.; Joule, J. A.; Murai, T.; Ramsden, C. A.

Authors: Aitken, R. A.; Glushkov, V.; González-Bello, C.; Kwiecien, H.; Mutoh, Y.; Nakata, M.; Saikawa, Y.; Shklyaev, Y.

Title: Knowledge Updates 2018/3

Print ISBN: 9783132423213; Online ISBN: 9783132423244; Book DOI: 10.1055/b-006-161208

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Faul, M.; Fürstner, A. (Editor-in-Chief); Kobayashi, S.; Koch, G.; Molander, G.; Nevado, C.; Trost, B. M.; You, S.

Type: Multivolume Edition

 

Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of isoquinolin-1(2H)-ones and isoquinolin-3(2H)-ones. The focus is on the literature published in the period 2005-2015, and includes new cyclization reactions, C-H activation methods, and catalysis by metal complexes of nickel, ruthenium, rhodium, and palladium.

 
  • 1 Chary RG, Dhananjaya G, Prasad KV, Vaishaly S, Ganesh YSS, Dulla B, Kumar KS, Pal M. Chem. Commun. (Cambridge) 2014; 50: 6797
  • 2 Ambalatharasu S, Sankar A, Peramaiyan G, Chakkaravarthi G, Kanagadurai R. Acta Crystallogr., Sect. E 2014; 70: o491
  • 3 Gerega A, Lapinski L, Nowak MJ, Furmanchuk A, Leszczynski J. J. Phys. Chem. A 2007; 111: 4934
  • 4 Yue S, Jiao Z-Z, Sun H-X, Jin T-Y, Xiang L. Helv. Chim. Acta 2015; 98: 961
  • 5 Jin Y-S, Du J-L, Yang Y, Jin L, Song Y, Zhang W, Chen H-S. Chem. Nat. Compd. (Engl. Transl.) 2011; 47: 257
  • 6 Jangir R, Gadre SR, Argade NP. Synthesis 2014; 46: 1954
  • 7 Müjde B, Özcan S, Balci M. Phytochem. Lett. 2011; 4: 407
  • 8 Teichert A, Schmidt J, Porzel A, Arnold N, Wessjohann L. J. Nat. Prod. 2008; 71: 1092
  • 9 Neuwoehner J, Reineke A-K, Hollender J, Eisentraeger A. Ecotoxicol. Environ. Saf. 2009; 72: 819
  • 10 Petrova R, Titorenkova R, Shivachev B. Acta Crystallogr., Sect. E 2007; 63: o475-1
  • 11 Manivel P, Hathwar VR, Subashini R, Nithya P, Khan FN. Acta Crystallogr., Sect. E 2009; 65: o261
  • 12 Ali FI, Babar TM, Rama NH, Jones PG. Acta Crystallogr., Sect. E 2010; 66: o16
  • 13 Said IM, Hamid NAA, Latif J, Din LB, Yamin BM. Acta Crystallogr., Sect. E 2005; 61: o797
  • 14 Salah HB, Kammoun M, Hamdi B, Bohé L, Damak M. Acta Crystallogr., Sect. E 2008; 64: o1050
  • 15 Khadka DB, Cho W-J. Bioorg. Med. Chem. 2011; 19: 724
  • 16 Khadka DB, Woo H, Yang SH, Zhao C, Jin Y, Le TN, Kwon Y, Cho W-J. Eur. J. Med. Chem. 2015; 92: 583
  • 17 Ryckebusch A, Garcin D, Lansiaux A, Goossens J-F, Baldeyrou B, Houssin R, Bailly C, Hénichart J-P. J. Med. Chem. 2008; 51: 3617
  • 18 Ahn G, Schifano-Faux N, Goossens J-F, Baldeyrou B, Couture A, Grandclaudon P, Lansiaux A, Ryckebusch A. Bioorg. Med. Chem. Lett. 2011; 21: 2259
  • 19 El Blidi L, Namoune A, Bridoux A, Nimbarte VD, Lawsson AM, Comesse S, Daïch A. Synthesis 2015; 47: 3583
  • 20 Lee S-H, Van HTM, Yang SH, Lee K-T, Kwon Y, Cho W-J. Bioorg. Med. Chem. Lett. 2009; 19: 2444
  • 21 Van HTM, Khadka DB, Yang SH, Le TN, Cho SH, Zhao C, Lee I-S, Kwon Y, Lee K-T, Kim Y-C, Cho W-J. Bioorg. Med. Chem. 2011; 19: 5311
  • 22 Morgan RK, Carter-O’Connell I, Cohen MS. Bioorg. Med. Chem. Lett. 2015; 25: 4770
  • 23 Branca D, Cerretani M, Jones P, Koch U, Orvieto F, Palumbi MC, Rowley M, Toniatti C, Muraglia E. Bioorg. Med. Chem. Lett. 2009; 19: 4042
  • 24 Peukert S, Schwahn U, Güssregen S, Schreuder H, Hofmeister A. Synthesis 2005; 1550
  • 25 Ray P, Wright J, Adam J, Boucharens S, Black D, Brown AR, Epemolu O, Fletcher D, Huggett M, Jones P, Laats S, Lyons A, de Man J, Morphy R, Sherborne B, Sherry L, van Straten N, Westwood P, York M. Bioorg. Med. Chem. Lett. 2011; 21: 1084
  • 26 Ginn JD, Bosanac T, Chen R, Cywin C, Hickey E, Kashem M, Kerr S, Kugler S, Li X, Prokopowicz III A, Schlyer S, Smith JD, Turner MR, Wu F, Young ERR. Bioorg. Med. Chem. Lett. 2010; 20: 5153
  • 27 Bosanac T, Hickey ER, Ginn J, Kashem M, Kerr S, Kugler S, Li X, Olague A, Schlyer S, Young ERR. Bioorg. Med. Chem. Lett. 2010; 20: 3746
  • 28 Hong J-B, Davidson JP, Jin Q, Lee GR, Matchett M, O’Brien E, Welch M, Bingenheimer B, Sarma K. Org. Process Res. Dev. 2014; 18: 228
  • 29 Zhao X, Xin M, Huang W, Ren Y, Jin Q, Tang F, Jiang H, Wang Y, Yang J, Mo S, Xiang H. Bioorg. Med. Chem. 2015; 23: 348
  • 30 Lou Y, Han X, Kuglstatter A, Kondru RK, Sweeney ZK, Soth M, McIntosh J, Litman R, Suh J, Kocer B, Davis D, Park J, Frauchiger S, Dewdney N, Zecic H, Taygerly JP, Sarma K, Hong J, Hill RJ, Gabriel T, Goldstein DM, Owens TD. J. Med. Chem. 2015; 58: 512
  • 31 Kang B-R, Shan A-L, Li Y-P, Xu J, Lu S-M, Zhang S-Q. Bioorg. Med. Chem. 2013; 21: 6956
  • 32 Alonso M, Chicharro R, Miranda C, Arán VJ, Maestro MA, Herradón B. J. Org. Chem. 2010; 75: 342
  • 33 Murray J, Giannetti AM, Steffek M, Gibbons P, Hearn BR, Cohen F, Tam C, Pozniak C, Bravo B, Lewcock J, Jaishankar P, Ly CQ, Zhao X, Tang Y, Chugha P, Arkin MR, Flygare J, Renslo AR. ChemMedChem 2014; 9: 73
  • 34 Dou D, Viwanathan P, Li Y, He G, Alliston KR, Lushington GH, Brown-Clay JD, Padmanabhan R, Groutas WC. J. Comb. Chem. 2010; 12: 836
  • 35 Asano Y, Kitamura S, Ohra T, Itoh F, Kajino M, Tamura T, Kaneko M, Ikeda S, Igata H, Kawamoto T, Sogabe S, Matsumoto S, Tanaka T, Yamaguchi M, Kimura H, Fukumoto S. Bioorg. Med. Chem. 2008; 16: 4699
  • 36 Velcicky J, Feifel R, Hawtin S, Heng R, Huppertz C, Koch G, Kroemer M, Moebitz H, Revesz L, Scheufler C, Schlapbach A. Bioorg. Med. Chem. Lett. 2010; 20: 1293
  • 37 Ortega R, Raviña E, Masaguer CF, Areias F, Brea J, Loza MI, López L, Selent J, Pastor M, Sanz F. Bioorg. Med. Chem. Lett. 2009; 19: 1773
  • 38 López L, Selent J, Ortega R, Masaguer CF, Domínguez E, Areias F, Brea J, Loza MI, Sanz F, Pastor M. ChemMedChem 2010; 5: 1300
  • 39 Ortega R, Hübner H, Gmeiner P, Masaguer CF. Bioorg. Med. Chem. Lett. 2011; 21: 2670
  • 40 Fevig JM, Feng J, Rossi KA, Miller KJ, Wu G, Hung C-P, Ung T, Malmstrom SE, Zhang G, Keim WJ, Cullen MJ, Rohrbach KW, Qu Q, Gan J, Pelleymounter MA, Robl JA. Bioorg. Med. Chem. Lett. 2013; 23: 330
  • 41 Zhou D, Gross JL, Adedoyin AB, Aschmies SB, Brennan J, Bowlby M, Di L, Kubek K, Platt BJ, Wang Z, Zhang G, Brandon N, Comery TA, Robichaud AJ. J. Med. Chem. 2012; 55: 2452
  • 42 Trabanco AA, Duvey G, Cid JM, Macdonald GJ, Cluzeau P, Nhem V, Furnani R, Behaj N, Poulain G, Finn T, Lavreysen H, Poli S, Raux A, Thollon Y, Poirier N, D’Addona D, Andrés JI, Lutjens R, Le Poul E, Imogai H, Rocher J-P. Bioorg. Med. Chem. Lett. 2011; 21: 971
  • 43 Xi B-M, Ni P-Z, Jiang Z-Z, Wu D-Q, Zhang S-H, Zhang H-B, Wang T, Chen W-H. Chem. Biol. Drug Des. 2010; 76: 505
  • 44 Abate C, Ferorelli S, Contino M, Marottoli R, Colabufo NA, Perrone R, Berardi F. Eur. J. Med. Chem. 2011; 46: 4733
  • 45 Abate C, Selivanova SV, Müller A, Krämer SD, Schibli R, Marottoli R, Perrone R, Berardi F, Niso M, Ametamey SM. Eur. J. Med. Chem. 2013; 69: 920
  • 46 Holzer P, Masuya K, Furet P, Kallen J, Valat-Stachyra T, Ferretti S, Berghausen J, Bouisset-Leonard M, Buschmann N, Pissot-Soldermann C, Rynn C, Ruetz S, Stuz S, Chène P, Jeay S, Gessier F. J. Med. Chem. 2015; 58: 6348
  • 47 Rothweiler U, Czarna A, Krajewski M, Ciombor J, Kalinski C, Khazak V, Ross G, Skobeleva N, Weber L, Holak TA. ChemMedChem 2008; 3: 1118
  • 48 Tang Z, Niu S, Liu F, Lao K, Miao J, Ji J, Wang X, Yan M, Zhang L, You Q, Xiao H, Xiang H. Bioorg. Med. Chem. Lett. 2014; 24: 2129
  • 49 Letourneau JJ, Liu J, Ohlmeyer MHJ, Riviello C, Rong Y, Li H, Appell KC, Bansal S, Jacob B, Wong A, Webb ML. Bioorg. Med. Chem. Lett. 2009; 19: 352
  • 50 Chen L, Conda-Sheridan M, Reddy PVN, Morrell A, Park E-J, Kondratyuk TP, Pezzuto JM, van Breemen RB, Cushman M. J. Med. Chem. 2012; 55: 5965
  • 51 Roth J, Madoux F, Hodder P, Roush WR. Bioorg. Med. Chem. Lett. 2008; 18: 2628
  • 52 Vikharev YuB, Shklyaev YuV, Anikina LV, Kolla VE, Tolstikov AG. Pharm. Chem. J. (Engl. Transl.) 2005; 39: 405
  • 53 Dieudonné-Vatran A, Azoulay M, Florent J-C. Org. Biomol. Chem. 2012; 10: 2683
  • 54 Chelucci G, Baldino S. Tetrahedron Lett. 2008; 49: 2738
  • 55 Okuro K, Alper H. Tetrahedron Lett. 2012; 53: 4816
  • 56 Zheng Z, Alper H. Org. Lett. 2008; 10: 4903
  • 57 Irudayanathan FM, Noh J, Choi J, Lee S. Adv. Synth. Catal. 2014; 356: 3433
  • 58 Grigg R, Elboray EE, Akkarasamiyo S, Chuanopparat N, Dondas HA, Abbas-Temirek HH, Fishwick CWG, Aly MF, Kongkathip B, Kongkathip N. Chem. Commun. (Cambridge) 2016; 52: 164
  • 59 Zhu C, Wang R, Falck JR. Chem.–Asian J. 2012; 7: 1502
  • 60 He R, Huang Z-T, Zheng Q-Y, Wang C. Tetrahedron Lett. 2014; 55: 5705
  • 61 Ackermann L. Acc. Chem. Res. 2014; 47: 281
  • 62 Manna S, Antonchik AP. Angew. Chem. 2014; 126: 7452 Angew. Chem. Int. Ed. 2014; 53: 7324
  • 63 Chen Z-W, Zhu Y-Z, Ou J-W, Wang Y-P, Zheng J-Y. J. Org. Chem. 2014; 79: 10 988
  • 64 Guastavino JF, Barolo SM, Rossi RA. Eur. J. Org. Chem. 2006; 3898
  • 65 Orito K, Horibata A, Nakamura T, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Tokuda M. J. Am. Chem. Soc. 2004; 126: 14 342
  • 66 Albert J, Ariza X, Calvet T, Font-Bardia M, Garcia J, Granell J, Lamela A, López B, Martinez M, Ortega L, Rodriguez A, Santos D. Organometallics 2013; 32: 649
  • 67 Vicente J, Saura-Llamas I, García-López J-A, Bautista D. Organometallics 2009; 28: 448
  • 68 Oliva-Madrid M-J, García-López J-A, Saura-Llamas I, Bautista D, Vicente J. Organometallics 2012; 31: 3647
  • 69 López B, Rodriguez A, Santos D, Albert J, Ariza X, Garcia J, Granell J. Chem. Commun. (Cambridge) 2011; 47: 1054
  • 70 Ren W, Yamane M. J. Org. Chem. 2010; 75: 8410
  • 71 Ren W, Yamane M. J. Org. Chem. 2009; 74: 8332
  • 72 Gross U, Koos P, O’Brien M, Polyzos A, Ley SV. Eur. J. Org. Chem. 2014; 6418
  • 73 Tyagi V, Khan S, Giri A, Gauniyal HM, Sridhar B, Chauhan PMS. Org. Lett. 2012; 14: 3126
  • 74 Kobayashi K, Hayashi K, Nam C, Fukamachi S, Konishi H. Heterocycles 2008; 75: 1225
  • 75 Le TN, Gang SG, Cho W-J. J. Org. Chem. 2004; 69: 2768
  • 76 Le TN, Cho W-J. Chem. Pharm. Bull. 2005; 53: 118
  • 77 Yang SH, Van HTM, Le TN, Khadka DB, Cho SH, Lee K-T, Lee E-S, Lee YB, Ahn C-H, Cho W-J. Eur. J. Med. Chem. 2010; 45: 5493
  • 78 Van HTM, Yang SH, Khadka DB, Kim Y-C, Cho W-J. Tetrahedron 2009; 65: 10 142
  • 79 Van HTM, Khadka DB, Le TN, Yang SH, Cho W-J. Chem. Pharm. Bull. 2011; 59: 1169
  • 80 Enders D, Braig V, Boudou M, Raabe G. Synthesis 2004; 2980
  • 81 Boudou M, Enders D. J. Org. Chem. 2005; 70: 9486
  • 82 Hahn R, Jafari E, Raabe G, Enders D. Synthesis 2015; 47: 472
  • 83 Wang L, Ren Z-L, Ding M-W. J. Org. Chem. 2015; 80: 641
  • 84 Duan Z, Gao Y, Yuan D, Ding M-W. Synlett 2015; 26: 2598
  • 85 Bunce RA, Nammalwar B, Gnanasekaran KK, Cain NR. Tetrahedron 2014; 70: 838
  • 86 Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4684
  • 87 Grigorjeva L, Daugulis O. Angew. Chem. 2014; 126: 10 373 Angew. Chem. Int. Ed. 2014; 53: 10 209
  • 88 Liu C-C, Parthasarathy K, Cheng C-H. Org. Lett. 2010; 12: 3518
  • 89 Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 14 952
  • 90 Kajita Y, Matsubara S, Kurahashi T. J. Am. Chem. Soc. 2008; 130: 6058
  • 91 Fujiwara K, Kurahashi T, Matsubara S. Org. Lett. 2010; 12: 4548
  • 92 Miura T, Yamauchi M, Murakami M. Org. Lett. 2008; 10: 3085
  • 93 Miura T, Morimoto M, Yamauchi M, Murakami M. J. Org. Chem. 2010; 75: 5359
  • 94 Fang Z-J, Zheng S-C, Guo Z, Guo J-Y, Tan B, Liu X-Y. Angew. Chem. 2015; 127: 9664 Angew. Chem. Int. Ed. 2015; 54: 9528
  • 95 Wang H, Yu S. Org. Lett. 2015; 17: 4272
  • 96 Wang F, Liu H, Fu H, Jiang Y, Zhao Y. Org. Lett. 2009; 11: 2469
  • 97 Shi Y, Zhu X, Mao H, Hu H, Zhu C, Cheng Y. Chem.–Eur. J. 2013; 19: 11 553
  • 98 Mayo MS, Yu X, Feng X, Yamamoto Y, Bao M. J. Org. Chem. 2015; 80: 3998
  • 99 Zhu W, Zhang D, Yang N, Liu H. Chem. Commun. (Cambridge) 2014; 50: 10 634
  • 100 Ackermann L, Lygin AV, Hofmann N. Angew. Chem. 2011; 123: 6503 Angew. Chem. Int. Ed. 2011; 50: 6379
  • 101 Deponti M, Kozhushkov SI, Yufit DS, Ackermann L. Org. Biomol. Chem. 2013; 11: 142
  • 102 Ackermann L, Fenner S. Org. Lett. 2011; 13: 6548
  • 103 Yang F, Ackermann L. J. Org. Chem. 2014; 79: 12 070
  • 104 Li B, Feng H, Xu S, Wang B. Chem.–Eur. J. 2011; 17: 12 573
  • 105 Patureau FW, Glorius F. Angew. Chem. 2011; 123: 2021 Angew. Chem. Int. Ed. 2011; 50: 1977
  • 106 Reddy MC, Manikandan R, Jeganmohan M. Chem. Commun. (Cambridge) 2013; 49: 6060
  • 107 Li B, Ma J, Wang N, Feng H, Xu S, Wang B. Org. Lett. 2012; 14: 736
  • 108 Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
  • 109 Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449
  • 110 Song G, Chen D, Pan C-L, Crabtree RH, Li X. J. Org. Chem. 2010; 75: 7487
  • 111 Mochida S, Umeda N, Hirano K, Satoh T, Miura M. Chem. Lett. 2010; 39: 744
  • 112 Hyster TK, Rovis T. J. Am. Chem. Soc. 2010; 132: 10 565
  • 113 Hyster TK, Rovis T. Synlett 2013; 24: 1842
  • 114 Hyster TK, Dalton DM, Rovis T. Chem. Sci. 2015; 6: 254
  • 115 Rakshit S, Grohmann C, Besset T, Glorius F. J. Am. Chem. Soc. 2011; 133: 2350
  • 116 Yu D-G, de Azambuja F, Glorius F. Angew. Chem. 2014; 126: 2792 Angew. Chem. Int. Ed. 2014; 53: 2754
  • 117 Ye B, Cramer N. Science (Washington, D. C.) 2012; 338: 504
  • 118 Wodrich MD, Ye B, Gonthier JF, Corminboeuf C, Cramer N. Chem.–Eur. J. 2014; 20: 15 409
  • 119 Hyster TK, Knörr L, Ward TR, Rovis T. Science (Washington, D. C.) 2012; 338: 500
  • 120 Xu L, Zhu Q, Huang G, Cheng B, Xia Y. J. Org. Chem. 2012; 77: 3017
  • 121 Guo W, Zhou T, Xia Y. Organometallics 2015; 34: 3012
  • 122 Quiñones N, Seoane A, García-Fandino R, Mascareñas JL, Gulías M. Chem. Sci. 2013; 4: 2874
  • 123 Yu B, Chen Y, Hong M, Duan P, Gan S, Chao H, Zhao Z, Zhao J. Chem. Commun. (Cambridge) 2015; 51: 14 365
  • 124 Su B, Wei J-B, Wu W-L, Shi Z-J. ChemCatChem 2015; 7: 2986
  • 125 Xu X, Liu Y, Park C-M. Angew. Chem. 2012; 124: 9506 Angew. Chem. Int. Ed. 2012; 51: 9372
  • 126 Yu D-G, de Azambuja F, Gensch T, Daniliuc CG, Glorius F. Angew. Chem. 2014; 126: 9804 Angew. Chem. Int. Ed. 2014; 53: 9650
  • 127 Wu Y, Sun P, Zhang K, Yang T, Yao H, Lin A. J. Org. Chem. 2016; 81: 2166
  • 128 Shi L, Yu K, Wang B. Chem. Commun. (Cambridge) 2015; 51: 17 277
  • 129 Zhang S-S, Wu J-Q, Liu X, Wang H. ACS Catal. 2015; 5: 210
  • 130 Webb NJ, Marsden SP, Raw SA. Org. Lett. 2014; 16: 4718
  • 131 Wang H, Glorius F. Angew. Chem. 2012; 124: 7430 Angew. Chem. Int. Ed. 2012; 51: 7318
  • 132 Cui S, Zhang Y, Wu Q. Chem. Sci. 2013; 4: 3421
  • 133 Liu H, An Z, He J. ACS Catal. 2014; 4: 3543
  • 134 Wang H, Grohmann C, Nimphius C, Glorius F. J. Am. Chem. Soc. 2012; 134: 19 592
  • 135 Presset M, Oehlrich D, Rombouts F, Molander GA. Org. Lett. 2013; 15: 1528
  • 136 Zhong H, Yang D, Wang S, Huang J. Chem. Commun. (Cambridge) 2012; 48: 3236
  • 137 Zhang N, Li B, Zhong H, Huang J. Org. Biomol. Chem. 2012; 10: 9429
  • 138 Lu S, Lin Y, Zhong H, Zhao K, Huang J. Tetrahedron Lett. 2013; 54: 2001
  • 139 Shu Z, Li W, Wang B. ChemCatChem 2015; 7: 605
  • 140 Xia X-F, Wang Y-Q, Zhang L-L, Song X-R, Liu X-Y, Liang Y-M. Chem.–Eur. J. 2014; 20: 5087
  • 141 Antczak MI, Ready JM. Chem. Sci. 2012; 3: 1450
  • 142 Cherry K, Duchêne A, Thibonnet J, Parrain J-L, Abarbri M. Synthesis 2005; 2349
  • 143 Potikha LM, Gutsul RM, Kovtunenko VA, Tolmachev AA. Chem. Heterocycl. Compd. (Engl. Transl.) 2010; 46: 457
  • 144 Rosenker KMG, Paquette WD, Johnston PA, Sharlow ER, Vogt A, Bakan A, Lazo JS, Wipf P. Bioorg. Med. Chem. 2015; 23: 2810
  • 145 Seitz W, Geneste H, Backfisch G, Delzer J, Graef C, Hornberger W, Kling A, Subkowski T, Zimmerman N. Bioorg. Med. Chem. Lett. 2008; 18: 527
  • 146 Saari R, Törmä J-C, Nevalainen T. Bioorg. Med. Chem. 2011; 19: 939
  • 147 Yao T, Larock RC. J. Org. Chem. 2005; 70: 1432
  • 148 Mehta S, Yao T, Larock RC. J. Org. Chem. 2012; 77: 10 938
  • 149 Varela-Fernández A, Varela JA, Saá C. Synthesis 2012; 44: 3285
  • 150 Jithunsa M, Ueda M, Aoi N, Sugita S, Miyoshi T, Miyata O. Synlett 2013; 24: 475
  • 151 Yang G, Zhang W. Org. Lett. 2012; 14: 268
  • 152 Prakash S, Muralirajan K, Cheng C-H. Chem. Commun. (Cambridge) 2015; 51: 13 362
  • 153 Gao H, Zhang J. Adv. Synth. Catal. 2009; 351: 85
  • 154 Zhang M, Zhang H-J, Ruan W, Wen T-B. Eur. J. Org. Chem. 2015; 5914
  • 155 Vasilevsky SF, Mikhailovskaya TF, Mamatyuk VI, Salnikov GE, Bogdanchikov GA, Manoharan M, Alabugin IV. J. Org. Chem. 2009; 74: 8106
  • 156 Heo I-J, Lee S-J, Cho C-W. Bull. Korean Chem. Soc. 2012; 33: 333
  • 157 Chen P-Y, Chen H-M, Chiang MY, Wang Y-F, Li S-R, Wang T-P, Wang E-C. Tetrahedron 2012; 68: 3030
  • 158 Brockhausen I, Benn M, Bhat S, Marone S, Riley JG, Montoya-Peleaz P, Vlahakis JZ, Paulsen H, Schutzbach JS, Szarek WA. Glycoconjugate J. 2006; 23: 525
  • 159 Chuang T-H, Wu P-L. J. Chin. Chem. Soc. (Taipei) 2006; 53: 413
  • 160 Fish PV, Barber CG, Brown DG, Butt R, Collis MG, Dickinson RP, Henry BT, Horne VA, Huggins JP, King E, O’Gara M, McCleverty D, McIntosh F, Phillips C, Webster R. J. Med. Chem. 2007; 50: 2341
  • 161 Wu F, Büttner FH, Chen R, Hickey E, Jakes S, Kaplita P, Kashem MA, Kerr S, Kugler S, Paw Z, Prokopowicz A, Shih C-K, Snow R, Young E, Cywin CL. Bioorg. Med. Chem. Lett. 2010; 20: 3235
  • 162 Filipponi P, Ostacolo C, Novellino E, Pellicciari R, Gioiello A. Org. Process Res. Dev. 2014; 18: 1345
  • 163 Moreau A, Couture A, Deniau E, Grandclaudon P. Eur. J. Org. Chem. 2005; 3437
  • 164 Lee AWM, Chan WH, Chan ETT. J. Chem. Soc., Perkin Trans. 1 1992; 309
  • 165 Wong YH, Ho MKC, Hu Y, New DC, He X, Pang H. WO 2008 092 292, 2008
  • 166 Zhou W, Ni S, Mei H, Han J, Pan Y. Org. Lett. 2015; 17: 2724
  • 167 Yu W, Hu P, Fan Y, Yu C, Yan X, Li X, Xu X. Org. Biomol. Chem. 2015; 13: 3308
  • 168 Qian P, Du B, Jiao W, Mei H, Han J, Pan Y. Beilstein J. Org. Chem. 2016; 12: 301
  • 169 Chern M-S, Li W-R. Tetrahedron Lett. 2004; 45: 8323
  • 170 Awuah E, Carpetta A. J. Org. Chem. 2010; 75: 5627
  • 171 Spicer JA, Lena G, Lyons DM, Huttunen KM, Miller CK, O’Connor PD, Bull M, Helsby N, Jamieson SMF, Denny WA, Ciccone A, Browne KA, Lopez JA, Rudd-Schmidt J, Voskoboinik I, Trapani JA. J. Med. Chem. 2013; 56: 9542
  • 172 Gao M, Wang M, Miller KD, Sledge GW, Zheng Q-H. Eur. J. Med. Chem. 2008; 43: 2211
  • 173 Grunewald GL, Romero FA, Chieu AD, Fincham KJ, Bhat SR, Criscione KR. Bioorg. Med. Chem. 2005; 13: 1261
  • 174 In J, Hwang S, Kim C, Seo JH, Kim S. Eur. J. Org. Chem. 2013; 965
  • 175 Kurouchi H, Kawamoto K, Sugimoto H, Nakamura S, Otani Y, Ohwada T. J. Org. Chem. 2012; 77: 9313
  • 176 Kurouchi H, Sumita A, Otani Y, Ohwada T. Chem.–Eur. J. 2014; 20: 8682
  • 177 Banwell MG, Cowden CJ, Gable RW. J. Chem. Soc., Perkin Trans. 1 1994; 3515
  • 178 Judd KE, Mahon MF, Caggiano L. Synthesis 2009; 2809
  • 179 Murashige R, Ohtsuka Y, Sagisawa K, Shiraishi M. Tetrahedron Lett. 2015; 56: 3410
  • 180 Raja EK, Lill SON, Klumpp DA. Chem. Commun. (Cambridge) 2012; 48: 8141
  • 181 Wei W-T, Liu Y, Ye L-M, Lei R-H, Zhang X-J, Yan M. Org. Biomol. Chem. 2015; 13: 817
  • 182 Feng C-L, Zhang S-G, Chen J-Q, Cai J, Ji M. Chin. Chem. Lett. 2013; 24: 767
  • 183 Chen W, Cui J, Zhu Y, Hu X, Mo W. J. Org. Chem. 2012; 77: 1585
  • 184 Majumdar KC, Chakravorty S, Ray K. Synthesis 2008; 2991
  • 185 Petrone DA, Yoon H, Weinstabl H, Lautens M. Angew. Chem. 2014; 126: 8042 Angew. Chem. Int. Ed. 2014; 53: 7908
  • 186 Ji F, Yi W-B, Sun M, Lv M-F, Cai C. Mol. Diversity 2013; 17: 295
  • 187 Thansandote P, Gouliaras C, Turcotte-Savard M-O, Lautens M. J. Org. Chem. 2009; 74: 1791
  • 188 Pedroni J, Saget T, Donets PA, Cramer N. Chem. Sci. 2015; 6: 5164
  • 189 Ladd CL, Belouin AV, Charette AB. J. Org. Chem. 2016; 81: 256
  • 190 Tsai T-H, Chung W-H, Chang J-K, Hsu R-T, Chang N-C. Tetrahedron 2007; 63: 9825
  • 191 Sośnicki JG, Struk . Synlett 2010; 1209
  • 192 Nieto-García O, Alonso R. J. Org. Chem. 2013; 78: 2564
  • 193 Frankowski KJ, Hirt EE, Zeng Y, Neuenswander B, Fowler D, Schoenen F, Aubé J. J. Comb. Chem. 2007; 9: 1188
  • 194 Korivi RP, Wu Y-C, Cheng C-H. Chem.–Eur. J. 2009; 15: 10 727
  • 195 Mohamed MA, Yamada K, Tomioka K. Tetrahedron Lett. 2009; 50: 3436
  • 196 Herter S, McKenna SM, Frazer AR, Leimkühler S, Carnell AJ, Turner NJ. ChemCatChem 2015; 7: 2313
  • 197 Bechi B, Herter S, McKenna S, Riley C, Leimkühler S, Turner NJ, Carnell AJ. Green Chem. 2014; 16: 4524
  • 198 Li C, Zeng C-C, Hu L-M, Yang F-L, Yoo SJ, Little RD. Electrochim. Acta 2013; 114: 560
  • 199 Khanzhin N, Juhl K, Nielsen SM, Simonsen KB. WO 2009 156 339, 2009
  • 200 Gitto R, Barreca ML, Francica E, Caruso R, De Luca L, Russo E, De Sarro G, Chimirri A. ARKIVOC 2004; v, 170
  • 201 Gitto R, Francica E, De Sarro G, Scicchitano F, Chimirri A. Chem. Pharm. Bull. 2008; 56: 181
  • 202 Stoyanova MP, Angelova SE, Kosev KS, Denkova PS, Enchev VG, Palamareva MD. Tetrahedron Lett. 2006; 47: 2119
  • 203 Sarnpitak P, Krasavin M. Tetrahedron Lett. 2014; 55: 2299
  • 204 Wang L, Liu J, Tian H, Qian C, Sun J. Adv. Synth. Catal. 2005; 347: 689
  • 205 Karimi AR, Momeni HR, Pashazadeh R. Tetrahedron Lett. 2012; 53: 3440
  • 206 Ghorbani-Choghamarani A, Hajjami M, Norouzi M, Abbasityula Y, Eigner V, Dušek M. Tetrahedron 2013; 69: 6541
  • 207 Karimi AR, Pashazadeh R. Synthesis 2010; 437
  • 208 Rudyanto M, Tomizawa Y, Morita H, Honda T. Org. Lett. 2008; 10: 1921
  • 209 Zhang S, Feng C, Cai J, Chen J, Ji M. J. Chem. Res. 2013; 291
  • 210 Cappelli A, Mohr GP, Giuliani G, Galeazzi S, Anzini M, Mennuni L, Ferrari F, Makovec F, Kleinrath EM, Langer T, Valoti M, Giorgi G, Vomero S. J. Med. Chem. 2006; 49: 6451
  • 211 Banno Y, Miyamoto Y, Sasaki M, Oi S, Asakawa T, Kataoka O, Takeuchi K, Suzuki N, Ikedo K, Kosaka T, Tsubotani S, Tani A, Funami M, Tawada M, Yamamoto Y, Aertgeerts K, Yano J, Maezaki H. Bioorg. Med. Chem. 2011; 19: 4953
  • 212 Roy S, Roy S, Neuenswander B, Hill D, Larock RC. J. Comb. Chem. 2009; 11: 1128
  • 213 Saeed A, Ashraf Z. Pharm. Chem. J. (Engl. Transl.) 2008; 42: 277
  • 214 Li DY, Shang XS, Chen GR, Liu PN. Org. Lett. 2013; 15: 3848
  • 215 Li DY, Shi KJ, Mao XF, Chen GR, Liu PN. J. Org. Chem. 2014; 79: 4602
  • 216 Buev EM, Moshkin VS, Sosnovskikh VY. Tetrahedron Lett. 2015; 56: 6590
  • 217 Jesudason CD, Beavers LS, Cramer JW, Dill J, Finley DR, Lindsley CW, Stevens FC, Gadski RA, Oldman SW, Pickard RT, Siedem CS, Sindelar DK, Singh A, Watson BM, Hipskind PA. Bioorg. Med. Chem. Lett. 2006; 16: 3415
  • 218 Shen Z, Ramamoorthy PS, Hatzenbuhler NT, Evrard DA, Childers W, Harrison BL, Chlenov M, Hornby G, Smith DL, Sullivan KM, Schechter LE, Andree TH. Bioorg. Med. Chem. Lett. 2010; 20: 222
  • 219 Ernst JT, Neubert T, Liu M, Sperry S, Zuccola H, Turnbull A, Fleck B, Kargo W, Woody L, Chiang P, Tran D, Chen W, Snyder P, Alcacio T, Nezami A, Reynolds J, Alvi K, Goulet L, Stamos D. J. Med. Chem. 2014; 57: 3382
  • 220 Frackenpohl J, Zeiβ H-J, Heinemann I, Willms L, Müller T, Busch M, Von Koskull-Döring P, Rosinger CH, Dittgen J, Hills MJ. WO 2013 004 652, 2013
  • 221 Torisawa Y, Aki S, Minamikawa J. Bioorg. Med. Chem. Lett. 2007; 17: 453
  • 222 Torisawa Y, Nishi T, Minamikawa J. Bioorg. Med. Chem. Lett. 2007; 17: 448
  • 223 Cai C, Plummer JS, Connor D, Holsworth DD, Edmunds JJ. Synth. Commun. 2005; 35: 349
  • 224 Tangallapally RP, Lee REB, Lenaerts AJM, Lee RE. Bioorg. Med. Chem. Lett. 2006; 16: 2584
  • 225 Watson NS, Adams C, Belton D, Brown D, Burns-Kurtis CL, Chaudry L, Chan C, Convery MA, Davies DE, Exall AM, Harling JD, Irvine S, Irving WR, Kleanthous S, McLay IM, Pateman AJ, Patikis AN, Roethke TJ, Senger S, Stelman GJ, Toomey JR, West RI, Whittaker C, Zhou P, Young RJ. Bioorg. Med. Chem. Lett. 2011; 21: 1588
  • 226 Reeves JT, Tan Z, Marsini MA, Han ZS, Xu Y, Reeves DC, Lee H, Lu BZ, Senanayake CH. Adv. Synth. Catal. 2013; 355: 47
  • 227 Lee S, Mah S, Hong S. Org. Lett. 2015; 17: 3864
  • 228 Nakao Y, Idei H, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2009; 131: 15 996
  • 229 Coote SC, Pöthig A, Bach T. Chem.–Eur. J. 2015; 21: 6906
  • 230 Sercel AD, Sanchez JP, Showalter HDH. Synth. Commun. 2007; 37: 4199
  • 231 Becknell NC, Lyons JA, Aimone LD, Gruner JA, Mathiasen JR, Raddatz R, Hudkins RL. Bioorg. Med. Chem. Lett. 2011; 21: 7076
  • 232 Rode HB, Sos ML, Grütter C, Heynck S, Simard JR, Rauh D. Bioorg. Med. Chem. 2011; 19: 429
  • 233 Fang Y-Q, Bio MM, Hansen KB, Potter MS, Clausen A. J. Am. Chem. Soc. 2010; 132: 15 525
  • 234 Kowalski P, Nowak K, Szpakiewicz B. J. Heterocycl. Chem. 2005; 42: 883
  • 235 Renaud J, Bischoff SF, Buhl T, Floersheim P, Fournier B, Geiser M, Halleux C, Kallen J, Keller H, Ramage P. J. Med. Chem. 2005; 48: 364
  • 236 Filipski KJ, Kohrt JT, Casimiro-Garcia A, Van Huis CA, Dudley DA, Cody WL, Bigge CF, Desiraju S, Sun S, Maiti SN, Jaber MR, Edmunds JJ. Tetrahedron Lett. 2006; 47: 7677
  • 237 Minter DE, Winslow CD. J. Org. Chem. 2004; 69: 1603
  • 238 Brookings D, Davenport RJ, Davis J, Galvin FCA, Lloyd S, Mack SR, Owens R, Sabin V, Wynn J. Bioorg. Med. Chem. Lett. 2007; 17: 562
  • 239 Brady RM, Khakham Y, Lessene G, Baell JB. Org. Biomol. Chem. 2011; 9: 656
  • 240 Lee H, Kang B, Lee S-I, Hong SH. Synlett 2015; 26: 1077
  • 241 Ouchi H, Kawata Y, Ono M, Morita Y, Yamamoto Y, Takahata H. Heterocycles 2004; 62: 491
  • 242 Cho D, Ahn J, De Castro KA, Ahn H, Rhee H. Tetrahedron 2010; 66: 5583
  • 243 Pellicciari R, Camaioni E, Costantino G, Formentini L, Sabbatini P, Venturoni F, Eren G, Bellocchi D, Chiarugi A, Moroni F. ChemMedChem 2008; 3: 914
  • 244 Fu L, Liu X, Ling C, Cheng J, Guo X, He H, Ding S, Yang Y. Bioorg. Med. Chem. Lett. 2012; 22: 814
  • 245 Ferraccioli R, Forni A. Eur. J. Org. Chem. 2009; 3161
  • 246 Che C, Li S, Yu Z, Li F, Xin S, Zhou L, Lin S, Yang Z. ACS Comb. Sci. 2013; 15: 202
  • 247 Chan WW, Lo S-F, Zhou Z, Yu W-Y. J. Am. Chem. Soc. 2012; 134: 13 565
  • 248 Méndez LJ, Cánepa AS, González MG, Bravo RD. Tetrahedron Lett. 2012; 53: 688
  • 249 Bagheri M, Karimkoshteh M. Iran. J. Catal. 2013; 3: 27
  • 250 Pati K, Liu R-S. Chem. Commun. (Cambridge) 2009; 5233
  • 251 Zheng ZB, Wang AX, Scola P, D’Andrea S. Synth. Commun. 2009; 39: 1264
  • 252 Lai P-S, Dubland JA, Sarwar MG, Chudzinski MG, Taylor MS. Tetrahedron 2011; 67: 7586
  • 253 Su B, Deng M, Wang Q. Adv. Synth. Catal. 2014; 356: 977
  • 254 Li L, Zhou B, Wang Y-H, Shu C, Pan Y-F, Lu X, Ye L-W. Angew. Chem. 2015; 127: 8363 Angew. Chem. Int. Ed. 2015; 54: 8245
  • 255 Zhou B, Li L, Ye L-W. Synlett 2016; 27: 493
  • 256 Arthuis M, Pontikis R, Florent J-C. J. Org. Chem. 2009; 74: 2234
  • 257 Koszelewski D, Cwiklak M, Ostaszewski R. Tetrahedron: Asymmetry 2012; 23: 1256
  • 258 Butini S, Gemma S, Campiani G, Franceschini S, Trotta F, Borriello M, Ceres N, Ros S, Coccone SS, Bernetti M, De Angelis M, Brindisi M, Nacci V, Fiorini I, Novellino E, Cagnotto A, Mennini T, Sandager-Nielsen K, Andreasen JT, Scheel-Kruger J, Mikkelsen JD, Fattorusso C. J. Med. Chem. 2009; 52: 151
  • 259 Cao D-K, Sreevidya TV, Botoshansky M, Golden G, Benedict JB, Kaftory M. CrystEngComm 2011; 13: 3181
  • 260 Szatmári I, Fülöp F. Synthesis 2011; 745