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Fused Heteroaromatic Rings via Metal-Mediated/Catalyzed Intramolecular C–H Activation: A Comprehensive Review

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Abstract

The present review highlights the most important recent contributions toward the synthesis of functionalized fused heteroaromatic rings via intramolecular C–H activation mediated or catalyzed by transition metals. This type of reaction constitutes a versatile strategy to obtain a great variety of fused heterocyclic systems through the formation of carbon–carbon (C–C) and C–heteroatom bonds from direct coupling between two adjacent C–H bonds or C–H/H–X bonds. The  revision is focused on the synthesis of fused heterocycles through two chemical processes: (1) metal-catalyzed intramolecular oxidative C–H activation, and (2) intramolecular C–H activation mediated by metallic Lewis acids.

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References

  1. Webb ME, Marquet A, Mendel RR, Rebeille F, Smith AG (2007) Nat Prod Rep 24:988–1008

    Article  CAS  PubMed  Google Scholar 

  2. Kim J, Movassaghi M (2009) Chem Soc Rev 38:3035–3050

    Article  CAS  PubMed  Google Scholar 

  3. Bagley MC, Dale JW, Merritt EA, Xiong X (2005) Chem Rev 105:685–714

    Article  CAS  PubMed  Google Scholar 

  4. Mishra A, Ma CQ, Bauerle P (2009) Chem Rev 109:1141–1276

    Article  CAS  PubMed  Google Scholar 

  5. Negishi E, De Meijere A (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley, New York

    Book  Google Scholar 

  6. De Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions, second completely revised and enlarged edition. Wiley, New York

    Book  Google Scholar 

  7. Ackermann L (2009) Modern arylation methods. Wiley, New York

    Book  Google Scholar 

  8. Corbet JP, Mignani G (2006) Chem Rev 106:2651–2710

    Article  CAS  PubMed  Google Scholar 

  9. Jana R, Pathak TP, Sigman MS (2011) Chem Rev 111:1417–1492

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  10. Muci AR, Buchwald SL (2002) Top Curr Chem 219:131–209

    Article  CAS  Google Scholar 

  11. Hartwig JF (1998) Angew Chem Int Ed 37:2046–2067

    Article  CAS  Google Scholar 

  12. Cacchi S, Fabrizi G (2005) Chem Rev 105:2873–2920

    Article  CAS  PubMed  Google Scholar 

  13. Lyons TW, Sanford MS (2010) Chem Rev 110:1147–1169

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  14. Ge J, Wang X, Liu T, Shi Z, Xiao Q, Yin D (2016) RSC Adv 6:19571–19575

    Article  CAS  Google Scholar 

  15. Beller EM, Bolm C (1998) Transition metals for organic synthesis, vol I. Willey, New York

    Book  Google Scholar 

  16. Ruiz-Castillo P, Buchwald SL (2016) Chem Rev 116:12564–12649

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  17. Shang X, Liu ZQ (2013) Chem Soc Rev 42:3253–3260

    Article  CAS  PubMed  Google Scholar 

  18. Kozhushkov SI, Ackermann L (2013) Chem Sci 4:886–896

    Article  CAS  Google Scholar 

  19. Yeung CS, Dong VM (2011) Chem Rev 111:1215–1292

    Article  CAS  PubMed  Google Scholar 

  20. Scheuermann CJ (2010) Chem Asian J 5:436–451

    Article  CAS  PubMed  Google Scholar 

  21. Chen X, Engle KM, Wang DH, Yu JQ (2009) Angew Chem Int Ed 48:5094–5115

    Article  CAS  Google Scholar 

  22. Sun CL, Li BJ, Shi ZJ (2010) Chem Commun 46:677–685

    Article  CAS  Google Scholar 

  23. Kakiuchi F, Chatani N (2003) Adv Synth Catal 345:1077–1101

    Article  CAS  Google Scholar 

  24. Colby DA, Bergman RG, Ellman JA (2010) Chem Rev 110:624–655

    Article  CAS  PubMed  Google Scholar 

  25. Daugulis O, Do HQ, Shabashov D (2009) Acc Chem Res 42:1074–1086

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  26. Sherman ES, Chemler SR, Tan TB, Gerlits O (2004) Org Lett 6:1573–1575

    Article  CAS  PubMed  Google Scholar 

  27. Li S, Wu J (2011) Org Lett 13:712–715

    Article  CAS  PubMed  Google Scholar 

  28. Cheung CW, Buchwald SL (2012) J Org Chem 77:7526–7537

    Article  CAS  PubMed  Google Scholar 

  29. Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2010) Chem Rev 110:890–931

    Article  CAS  PubMed  Google Scholar 

  30. Moselage M, Li J, Ackermann L (2016) ACS Catal 6:498–525

    Article  CAS  Google Scholar 

  31. Planas O, Chirila PG, Whiteoak CJ, Riba X (2018) Adv Organomet Chem 69:209–282

    Article  Google Scholar 

  32. Wu X, Yang K, Zhao Y, Sun H, Li G, Ge H (2015) Nat Commun 6(6462):1–10

    Google Scholar 

  33. Fujioka T, Nakamura T, Yorimitsu H, Oshima K (2004) Org Lett 4:2257–2259

    Article  CAS  Google Scholar 

  34. Santhoshkumar R, Mannathan S, Cheng CH (2014) Org Lett 16:4208–4211

    Article  CAS  PubMed  Google Scholar 

  35. Wu C, Yoshikai N (2018) Angew Chem Int Ed 57:6558–6562

    Article  CAS  Google Scholar 

  36. Zhang Z, Li J, Zhang G, Ma N, Liu Q, Liu T (2015) J Org Chem 80:6875–6884

    Article  CAS  PubMed  Google Scholar 

  37. Jiang H, Yao W, Cao H, Huang H, Cao D (2010) J Org Chem 75:5347–5350

    Article  CAS  PubMed  Google Scholar 

  38. Nguyen Q, Nguyen T, Driver TG (2013) J Am Chem Soc 135:620–623

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  39. Yan Q, Luo J, Zhang-Negrerie D, Li H, Qi X, Zhao K (2011) J Org Chem 76:8690–8697

    Article  CAS  PubMed  Google Scholar 

  40. Ohashi M, Ikawa M, Ogoshi S (2011) Organometallics 30:2765–2774

    Article  CAS  Google Scholar 

  41. Egi M, Azechi K, Akai S (2009) Org Lett 11:5002–5005

    Article  CAS  PubMed  Google Scholar 

  42. Cho SH, Kim JY, Lee SY, Chang S (2009) Angew Chem Int Ed 48:9127–9130

    Article  CAS  Google Scholar 

  43. Fairlamb IJS (2007) Chem Soc Rev 36:1036–1045

    Article  CAS  PubMed  Google Scholar 

  44. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174–238

    Article  CAS  PubMed  Google Scholar 

  45. Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36:1173–1193

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  46. Ackermann L, Vicente R, Kapdi AR (2009) Angew Chem Int Ed 48:9792–9826

    Article  CAS  Google Scholar 

  47. Campeau LC, Fagnou K (2007) Chem Soc Rev 36:1058–1068

    Article  CAS  PubMed  Google Scholar 

  48. Bellina F, Rossi R (2009) Tetrahedron 65:10269–10310

    Article  CAS  Google Scholar 

  49. Hirano K, Miura M (2011) Synlett 2011:294–307

    Article  CAS  Google Scholar 

  50. Zhao X, Yu Z (2008) J Am Chem Soc 130:8136–8137

    Article  CAS  PubMed  Google Scholar 

  51. Wang C, Piel I, Glorius F (2009) J Am Chem Soc 131:4194–4195

    Article  CAS  PubMed  Google Scholar 

  52. Wang Z, Ni JZ, Kuninobu Y, Kanai M (2014) Angew Chem Int Ed 53:3496–3499

    Article  CAS  Google Scholar 

  53. Nishino M, Hirano K, Satoh T, Miura M (2011) J Org Chem 76:6447–6451

    Article  CAS  PubMed  Google Scholar 

  54. Tang L, Pang Y, Yan Q, Shi L, Du Y, Zhao K (2011) J Org Chem 76:2744–2752

    Article  CAS  PubMed  Google Scholar 

  55. Li C, Zhang Y, Li P, Wang L (2011) J Org Chem 76:4692–4696

    Article  CAS  PubMed  Google Scholar 

  56. Jana S, Clements MD, Sharp BK, Zheng N (2010) Org Lett 12:3736–3739

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  57. Wurz S, Rakshit S, Neumann JJ, Droge T, Glorius F (2008) Angew Chem Int Ed 47:7230–7233

    Article  CAS  Google Scholar 

  58. Neumann JJ, Rakshit S, Droge T, Wurz S, Glorius F (2011) Chem Eur J 17:7298–7303

    Article  CAS  PubMed  Google Scholar 

  59. Bernini R, Fabrizi G, Stefarazza A, Cacchi S (2009) Angew Chem Int Ed 48:8078–8081

    Article  CAS  Google Scholar 

  60. Yu W, Du Y, Zhao K (2009) Org Lett 11:2417–2420

    Article  CAS  PubMed  Google Scholar 

  61. Guan ZH, Yan ZY, Ren ZH, Liua XY, Liang YM (2010) Chem Commun 46:2823–2825

    Article  CAS  Google Scholar 

  62. Wei Y, Deb I, Yoshikai N (2012) J Am Chem Soc 134:9098–9101

    Article  CAS  PubMed  Google Scholar 

  63. Guru MM, Ali MA, Punniyamurthy T (2011) J Org Chem 76:5295–5308

    Article  CAS  PubMed  Google Scholar 

  64. Peng J, Chen T, Chen C, Li B (2011) J Org Chem 76:9507–9513

    Article  CAS  PubMed  Google Scholar 

  65. Ma B, Wang Y, Peng J, Zhu Q (2011) J Org Chem 76:6362–6366

    Article  CAS  PubMed  Google Scholar 

  66. Inamoto K, Hasegawa C, Hiroya K, Doi T (2008) Org Lett 10:5147–5150

    Article  CAS  PubMed  Google Scholar 

  67. Inamoto K, Arai Y, Hiroya K, Doi T (2008) Chem Commun 2008:5529–5531

    Article  CAS  Google Scholar 

  68. Kumar RK, Ali MA, Punniyamurthy T (2011) Org Lett 13:2102–2105

    Article  CAS  PubMed  Google Scholar 

  69. Huang L, Niu T, Wu J, Zhang Y (2011) J Org Chem 76:1759–1766

    Article  CAS  PubMed  Google Scholar 

  70. Ghobrial M, Schnurch M, Mihovilovic MD (2011) J Org Chem 76:8781–8793

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  71. Li Y, Xie Y, Rong Z, Jin K, Wang X, Duan C (2011) J Org Chem 76:5444–5449

    Article  CAS  PubMed  Google Scholar 

  72. Monguchi D, Fujiwara T, Furukawa H, Mori A (2009) Org Lett 11:1607–1610

    Article  CAS  PubMed  Google Scholar 

  73. Inamoto K, Saito T, Katsuno M, Sakamoto T, Hiroya K (2007) Org Lett 9:2931–2934

    Article  CAS  PubMed  Google Scholar 

  74. Tsang WCP, Munday RH, Brasche G, Zheng N, Buchwald SL (2008) J Org Chem 73:7603–7610

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  75. Jordan-Hore JA, Johansson CCC, Gulias M, Beck EM, Gaunt MJ (2008) J Am Chem Soc 130:16184–16186

    Article  CAS  PubMed  Google Scholar 

  76. Fristad WE, Peterson JR (1985) Synth Commun 15:1–5

    Article  CAS  Google Scholar 

  77. Wallace TJ (1964) J Am Chem Soc 86:2018–2021

    Article  CAS  Google Scholar 

  78. Yiannios CN, Karabinos JV (1963) J Org Chem 28:3246–3248

    Article  CAS  Google Scholar 

  79. Arterburn JB, Perry MC, Nelson SL, Dible BR, Holguin MS (1997) J Am Chem Soc 119:9309–9310

    Article  CAS  Google Scholar 

  80. Cervilla A, Corma A, Fornes V, Llopis E, Palanca P, Rey F, Ribera A (1994) J Am Chem Soc 116:1595–1596

    Article  CAS  Google Scholar 

  81. Aoda T, Akasaka T, Furukawa N, Oae S (1976) Bull Chem Soc Jpn 49:1441–1442

    Article  Google Scholar 

  82. Zhang Z, Zhang J, Tan J, Wang Z (2008) J Org Chem 73(13):5180–5182

    Article  CAS  PubMed  Google Scholar 

  83. Wasa M, Yu JQ (2008) J Am Chem Soc 130(43):14058–114059

    Article  CAS  PubMed  Google Scholar 

  84. Majumdar KC, Samanta S, Nandi RK (2010) Tetrahedron Lett 51(29):3807–3900

    Article  CAS  Google Scholar 

  85. Xiao B, Gong TJ, Liu ZJ, Liu JH, Luo DF, Xu J, Liu L (2011) J Am Chem Soc 133:9250–9253

    Article  CAS  PubMed  Google Scholar 

  86. Youn SW, Bihn JH, Kim BS (2011) Org Lett 13:3738–3741

    Article  CAS  PubMed  Google Scholar 

  87. Wei Y, Yoshikai N (2011) Org Lett 13:5504–5507

    Article  CAS  PubMed  Google Scholar 

  88. Giri R, Liang J, Lei JG, Li JJ, Wang DH, Chen X, Naggar IC, Guo C, Foxman BM, Yu JQ (2005) Angew Chem Int Ed 44:7420–7424

    Article  CAS  Google Scholar 

  89. Muniz K (2009) Angew Chem Int Ed 48:9412–9423

    Article  CAS  Google Scholar 

  90. Yang G, Zhang W (2012) Org Lett 14(1):268–271

    Article  CAS  PubMed  Google Scholar 

  91. Weinstein AB, Stahl SS (2014) Catal Sci Technol 4:4301–4307

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  92. Oloo W, Zavalij PY, Zhang J, Khaskin E, Vedernikov AN (2010) J Am Chem Soc 132:14400–14402

    Article  CAS  PubMed  Google Scholar 

  93. Vedernikov AN (2012) Acc Chem Res 45:803–813

    Article  CAS  PubMed  Google Scholar 

  94. Vickers CJ, Mei TS, Yu JQ (2010) Org Lett 12:2511–2514

    Article  CAS  PubMed  Google Scholar 

  95. Shan G, Yang XL, Ma LL, Rao Y (2012) Angew Chem Int Ed 51:13070–13074

    Article  CAS  Google Scholar 

  96. Sharma A, Hartwig JF (2013) J Am Chem Soc 135:17983–17989

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  97. Zhu HT, Chen PH, Liu GS (2014) J Am Chem Soc 136:1766–1769

    Article  CAS  PubMed  Google Scholar 

  98. Stahl SS, Thorman JL, Nelson RC, Kozee MA (2001) J Am Chem Soc 123:7188–7189

    Article  CAS  PubMed  Google Scholar 

  99. Steinhoff BA, Fix SR, Stahl SS (2002) J Am Chem Soc 124:766–767

    Article  CAS  PubMed  Google Scholar 

  100. Nishimura T, Onoue T, Ohe K, Uemura S (1999) J Org Chem 64:6750–6755

    Article  CAS  PubMed  Google Scholar 

  101. Yang W, Chen J, Huang X, Ding J, Liu M, Wu H (2014) Org Lett 16:5418–5421

    Article  CAS  PubMed  Google Scholar 

  102. Choi S, Chatterjee T, Choi WJ, You Y, Choa EJ (2015) ACS Catal. 5:4796–4802

    Article  CAS  Google Scholar 

  103. Clagg K, Hou H, Weinstein AB, Russell D, Stahl SS, Koenig SG (2016) Org Lett 18:3586–3589

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  104. Lee DJ, Yoo EJ (2015) Org Lett 17:1830–1833

    Article  CAS  PubMed  Google Scholar 

  105. El-Atawy MA, Ferretti F, Ragaini F (2017) Eur J Org Chem 2017:1902–1910

    Article  CAS  Google Scholar 

  106. Ferretti F, El-Atawy MA, Muto S, Hagar M, Gallo E, Ragaini F (2015) Eur J Org Chem 2015:5712–5715

    Article  CAS  Google Scholar 

  107. Ueda S, Nagasawa H (2008) Angew Chem Int Ed 47:6411–6413

    Article  CAS  Google Scholar 

  108. Brasche G, Buchwald SL (2008) Angew Chem Int Ed 47:1932–1934

    Article  CAS  Google Scholar 

  109. Ley SV, Thomas AW (2003) Angew Chem Int Ed 2003(42):5400–5449

    Article  CAS  Google Scholar 

  110. Yamada K, Kubo T, Tokuyama H, Fukuyama T (2002) Synlett 2012:231–234

    Article  Google Scholar 

  111. Gillespie KM, Crust EJ, Deeth RJ, Scott P (2001) Chem Commun 2001:785–786

    Article  Google Scholar 

  112. Brandt P, Sndergren MJ, Andersson PG, Norrby PO (2000) J Am Chem Soc 122:8013–8020

    Article  CAS  Google Scholar 

  113. Li Z, Quan RW, Jacobsen EN (1995) J Am Chem Soc 117:5889–5890

    Article  CAS  Google Scholar 

  114. Sherman ES, Chemler SR (2009) Adv Synth Catal 351(3):467–471

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  115. S. Chiba

  116. Wang H, Wang Y, Peng C, Zhang J, Zhu Q (2010) J Am Chem Soc 132:13217–13219

    Article  CAS  PubMed  Google Scholar 

  117. Wang HG, Wang Y, Liang DD, Liu LY, Zhang JC, Zhu Q (2011) Angew Chem Int Ed 50(25):5678–5681

    Article  CAS  Google Scholar 

  118. Wang X, Jin Y, Zhao Y, Zhu L, Fu H (2012) Org Lett 14:452–455

    Article  CAS  PubMed  Google Scholar 

  119. Li X, He L, Chen H, Wu W, Jiang J (2013) J Org Chem 78:3636–3646

    Article  CAS  PubMed  Google Scholar 

  120. Takamatsu K, Hirano K, Satoh T, Miura M (2014) Org Lett 16:2892–2895

    Article  CAS  PubMed  Google Scholar 

  121. Liwosz TW, Chemler DSR (2014) Synlett 26:335–339

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  122. Lu JY, Jin YB, Liu HX, Jiang YY, Fu H (2011) Org Lett 13(14):3694–3697

    Article  CAS  PubMed  Google Scholar 

  123. Chen H, Sanjaya S, Wang YF, Chiba S (2013) Org Lett 15(1):212–215

    Article  CAS  PubMed  Google Scholar 

  124. Zhang T, Bao W (2013) J Org Chem 78:1317–1322

    Article  CAS  PubMed  Google Scholar 

  125. Liu Y, Chen GQ, Tse CW, Guan X, Xu XJ, Huang JS, Che CM (2015) Chem Asian J 10(1):100–105

    Article  CAS  PubMed  Google Scholar 

  126. Karthikeyan I, Sekar G (2014) Eur J Org Chem 2014(36):8055–8063

    Article  CAS  Google Scholar 

  127. Xu H, Fu H (2012) Chem Eur J 18:1180–1186

    Article  CAS  PubMed  Google Scholar 

  128. Chen DB, Chen QF, Liu MC, Dai S, Huang L, Yang J, Bao W (2013) Tetrahedron 69(31):6461–6467

    Article  CAS  Google Scholar 

  129. Berrino R, Cacchi S, Fabrizi G, Goggiamani A (2012) J Org Chem 77(5):2537–2542

    Article  CAS  PubMed  Google Scholar 

  130. Gui QW, Yang ZY, Chen X et al (2013) Synlett 24(8):1016–1020

    Article  CAS  Google Scholar 

  131. Huang J, Mao T, Zhu Q (2014) Eur J Org Chem. https://doi.org/10.1002/ejoc.201400012

    Article  Google Scholar 

  132. Chang HT, Jeganmohan M, Cheng CH (2007) Org Lett 9(3):505–508

    Article  CAS  PubMed  Google Scholar 

  133. Suzuki C, Hirano K, Satoh T, Miura M (2015) Org Lett 17:1597–1600

    Article  CAS  PubMed  Google Scholar 

  134. Matsubara S, Asano K, Kajita Y, Yamamoto M (2007) Synthesis 2007:2055

    Article  CAS  Google Scholar 

  135. Yamamoto M, Matsubara S (2007) Chem Lett 36:172–173

    Article  CAS  Google Scholar 

  136. Liegault B, Lee D, Huestis MP, Stuart DR, Fagnou K (2008) J Org Chem 73:5022–5028

    Article  CAS  PubMed  Google Scholar 

  137. Ackermann L, Jeyachandran R, Potukuchi HK, Novak P, Buttner L (2010) Org Lett 12:2056–2059

    Article  CAS  PubMed  Google Scholar 

  138. Xia XF, Wang N, Zhang LL, Song XR, Liu XY, Liang YM (2012) J Org Chem 77:9163–9170

    Article  CAS  PubMed  Google Scholar 

  139. Shi Z, Glorius F (2012) Angew Chem Int Ed 51:9220–9222

    Article  CAS  Google Scholar 

  140. Wang K, Lü M, Yu A, Zhu X, Wang Q (2009) J Org Chem 74:935–938

    Article  CAS  PubMed  Google Scholar 

  141. Wertz S, Leifert D, Studer A (2013) Org Lett 15:928–931

    Article  CAS  PubMed  Google Scholar 

  142. Guo X, Yu R, Li H, Li Z (2009) J Am Chem Soc 131:17387

    Article  CAS  PubMed  Google Scholar 

  143. Ding Z, Yoshikai N (2013) Angew Chem Int Ed 52:8574–8578. https://doi.org/10.1002/anie.201305151

    Article  CAS  Google Scholar 

  144. Fallon BJ, Derat E, Amatore M, Aubert C, Chemla F, Ferreira F, Perez-Luna A, Petit M (2016) Org Lett 18:2292–2295. https://doi.org/10.1021/acs.orglett.6b00939

    Article  CAS  PubMed  Google Scholar 

  145. Tobisu M, Koh K, Furukawa T, Chatani N (2012) Angew Chem Int Ed 51:11363–11366

    Article  CAS  Google Scholar 

  146. Wang Y, Zhang P, Di X, Dai Q, Zhang ZM, Zhang J (2017) Angew Chem Int Ed 56:15905–15909

    Article  CAS  Google Scholar 

  147. Peng AY, Ding YX (2003) J Am Chem Soc 2003(125):15006–15007

    Article  CAS  Google Scholar 

  148. Peng AY, Ding YX (2005) Org Lett 7(15):3299–3301

    Article  CAS  PubMed  Google Scholar 

  149. Ruppel JV, Kamble RM, Zhang XP (2007) Org Lett 9(23):4889–4892

    Article  CAS  PubMed  Google Scholar 

  150. Shen MH, Driver TG (2008) Org Lett 10(15):3367–3370

    Article  CAS  PubMed  Google Scholar 

  151. Tan Y, Hartwig JF (2010) J Am Chem Soc 132:3676–3677

    Article  CAS  PubMed  Google Scholar 

  152. Bonnamour J, Bolm C (2011) Org Lett 13:2012–2014

    Article  CAS  PubMed  Google Scholar 

  153. Deb I, Yoshikai N (2013) Org Lett 15:4254–4257

    Article  CAS  PubMed  Google Scholar 

  154. Shu C, Liu R, Liu S, Li JQ, Yu YF, He Q, Lu X, Ye LW (2014) Chem Asian J 9:1–6

    Article  CAS  Google Scholar 

  155. Gao WC, Liu T, Cheng YF, Chang HH, Li X, Zhou R, Wei WL, Qiao Y (2017) J Org Chem 82:13459–13467

    Article  CAS  PubMed  Google Scholar 

  156. Mun HJ, Seong EY, Ahn KH, Kang EJ (2018) J Org Chem 83:1196–1203

    Article  CAS  PubMed  Google Scholar 

  157. Yao B, Li Y, Liang Z, Zhang Y (2011) Org Lett 13:640–643

    Article  CAS  PubMed  Google Scholar 

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The author thank the Facultad de Farmacia (Universidad Central de Venezuela) for bibliography material and financial support.

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Romero, A.H. Fused Heteroaromatic Rings via Metal-Mediated/Catalyzed Intramolecular C–H Activation: A Comprehensive Review. Top Curr Chem (Z) 377, 21 (2019). https://doi.org/10.1007/s41061-019-0246-3

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