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Synthetic approaches to 4-(het)aryl-3,4-dihydroquinolin-2(1H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

This review summarizes strategies for the synthesis of 4-(het)aryl-3,4-dihydroquinolin-2(1H)-ones which are of interest due to their biological activity. It covers methods elaborated particularly for obtaining the title heterocycles, as well as procedures where these compounds are formed as side products. 4-Aryl-3,4-dihydroquinolin-2(1H)-one derivatives have been used for the synthesis of valuable molecules, e.g., anticancer drug tipifarnib.

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References

  1. Peng, W.-W.; Zeng, G.-Z.; Song, W.-W.; Tan, N.-H. Chem. Biodiversity 2013, 10, 1317.

    Article  CAS  Google Scholar 

  2. An, C.-Y.; Li, X.-M.; Luo, H.; Li, C.-S.; Wang, M.-H.; Xu, G.-M.; Wang, B.-G. J. Nat. Prod. 2013, 76, 1896.

    Article  CAS  Google Scholar 

  3. Chen, M.; Shao, C.-L.; She, Z.-G.; Wang, C.-Y. J. Nat. Prod. 2014, 77, 2720.

    Article  CAS  Google Scholar 

  4. Uchida, R.; Imasato, R.; Tomoda, H.; Omura, S. J. Antibiot. 2006, 59, 652.

    Article  CAS  Google Scholar 

  5. Larsen, T. O.; Smedsgaard, J.; Frisvad, J. C.; Anthoni, U.; Christophersen, C. Biochem. Syst. Ecol. 1999, 27, 329.

    Article  CAS  Google Scholar 

  6. Luqman, S.; Meena, A.; Singh, P.; Jondratyuk, T. P.; Marler, L. E.; Pezzuto, J. M.; Negi, A. S. Chem. Biol. Drug Des. 2012, 80, 616.

    Article  CAS  Google Scholar 

  7. Singer, J. M.; Barr, B. M.; Coughenour, L. L.; Gregory, T. F.; Walters, M. A. Bioorg. Med. Chem. Lett. 2005, 15, 4560.

    Article  CAS  Google Scholar 

  8. Mieriņa, I.; Stikute, A.; Jure, M. Chem. Heterocycl. Compd. 2014, 50, 1137. [Khim. Geterotsikl. Soedin. 2014, 1232.]

  9. Krapcho, J.; Schwartz, J.; Squibb, E. R. US Patent 3994900.

  10. Ozturk, T.; McKillop, A. Can. J. Chem. 2000, 78, 1158.

    Article  CAS  Google Scholar 

  11. Kraus, J. M.; Tatipaka, H. B.; McGuffin, S. A.; Chennamaneni, N. K.; Karimi, M.; Arif, J.; Verlinde, C. L. M. J.; Buckner, F. S.; Gelb, M. H. J. Med. Chem. 2010, 53, 3887.

    Article  CAS  Google Scholar 

  12. Angibaud, P. R.; Venet, M. G.; Filliers, W.; Broeckx, R.; Ligny, Y. A.; Muller, P.; Poncelet, V. S.; End, D. W. Eur. J. Org. Chem. 2004, 479.

  13. Safina, L. Yu.; Selivanova, G. A.; Koltunov, K. Yu.; Shteingarts, V. D. Tetrahedron Lett. 2009, 50, 5245.

    Article  CAS  Google Scholar 

  14. Zakusilo, D. N.; Ryabukhin, D. S.; Boyarskaya, I. A.; Yuzikhin, O. S.; Vasiliyev, A. V. Tetrahedron 2015, 71, 102.

    Article  CAS  Google Scholar 

  15. Singh, P.; Faridi, U.; Srivastava, S.; Kumar, J. K.; Darokar, M. P.; Liqman, S.; Shanker, K.; Chanotiya, C. S.; Gupta, A.; Gupta, M. M.; Negi, A. S. Chem. Pharm. Bull. 2010, 58, 242.

    Article  CAS  Google Scholar 

  16. Li, K.; Foresee, L. N.; Tunge, J. A. J. Org. Chem. 2005, 70, 2881.

    Article  CAS  Google Scholar 

  17. Wang, W.-F.; Fan, J.; Luo, C.-Z.; Yuan, Y.-F.; Zhang, Y.-F. ARKIVOC 2011, (xi), 105.

  18. Hansen, U.; Schaus, S.; Grant, T.; Bishop, J.; Kavouris, J.; Cristadore, L. M. WO Patent 2012050985.

  19. Conley, R. T.; Knopka, W. N. J. Org. Chem. 1964, 29, 496.

    Article  CAS  Google Scholar 

  20. Neugebauer, R. C.; Uchiechowska, U.; Meier, R.; Hruby, H.; Valkov, V.; Verdin, E.; Sippl, W.; Jung, M. J. Med. Chem. 2008, 51, 1203.

    Article  CAS  Google Scholar 

  21. Thirumurugan, R.; Shanmuga Sundara Raj, S.; Murugan, P.; Ramakrishnan, V. T.; Chacko, K. K. Acta Crystallogr. 1997, C53, 1862.

  22. Guan, L.-P.; Jin, Q.-H.; Tian, G.-R.; Chai, K.-Y.; Quan, Z.-S. J. Pharm. Pharm. Sci. 2007, 10, 254.

    CAS  Google Scholar 

  23. Lansbury, P. T., Jr.; Justman, C. J.; Grammatopoulos, T. N.; Lynch, B. A.; Liu, Z. US Patent 20110060005.

  24. Lansbury, P. T., Jr.; Justman, C. J.; Grammatopoulos, T. N.; Lynch, B. A.; Liu, Z. US Patent 20100331363.

  25. Lansbury, P. T., Jr.; Justman, C.; Meray, R. K.; Duggan, M. E.; Grammatopoulos, T.; Lynch, B.; Friedenburg, R. A.; Cullen, V. C.; Liu, Z. WO Patent 2010057028.

  26. Johnston, K. M. J. Heterocycl. Chem. 1969, 6, 847.

    Article  CAS  Google Scholar 

  27. Johnston, K. M. Tetrahedron 1968, 24, 5595.

    Article  CAS  Google Scholar 

  28. Kaboudin, B.; Abedi, Y. Org. Prep. Proced. Int. 2009, 41, 229.

    Article  CAS  Google Scholar 

  29. Koltunov, K. Yu.; Walspurger, S.; Sommer, J. Chem. Commun. 2004, 1754.

  30. Lee, E.; Han, S.; Jin, G. H.; Lee, H. J.; Kim, W.-Y.; Ryu, J.-H.; Jeon, R. Bioorg. Med. Chem. Lett. 2013, 23, 3976.

    Article  CAS  Google Scholar 

  31. Ellion, M. C.; Wordingham, S. V. Synlett 2004, 898.

  32. Davis, J. M.; Gregory, T. F.; Walters, M. A. WO Patent 2004029048.

  33. King, F. D.; Caddick, S. Tetrahedron 2013, 69, 487.

    Article  CAS  Google Scholar 

  34. Patil, D. V.; Cavitt, M. A.; Grzybowski, P.; France, S. Chem. Commun. 2012, 48, 10337.

    Article  CAS  Google Scholar 

  35. Angibaud, P.; Bourdrez, X.; Devine, A.; End, D. W.; Freyne, E.; Ligny, Y.; Muller, P; Mannens, G.; Pilatte, I.; Poncelet, V.; Skrzat, S.; Smets, G.; Van Dum, J.; Van Remoortee, P.; Venet, M.; Wouters, W. Bioorg. Med. Chem. Lett. 2003, 13, 1543.

    Article  CAS  Google Scholar 

  36. Schmutz, J.; Kuenzie, F. Helv. Chim. Acta 1970, 53, 89.

    Article  CAS  Google Scholar 

  37. King, F. D.; Caddick, S. Tetrahedron 2013, 69, 8592.

    Article  CAS  Google Scholar 

  38. King, F. D.; Aliev, A. E.; Caddick, S.; Tocher, D. A. J. Org. Chem. 2013, 78, 10938.

    Article  CAS  Google Scholar 

  39. Hajra, S.; Maji, B.; Karmakar, A. Tetrahedron Lett. 2005, 46, 8599.

    Article  CAS  Google Scholar 

  40. Fabry, D. C.; Stodulski, M.; Hoerner, S.; Gulder, T. Chem.–Eur. J. 2012, 18, 10834.

    Article  CAS  Google Scholar 

  41. Sun, B.; Mai, W.-P.; Yang, L.-R.; Mao, P.; Yuan, J.-W.; Xiao, Y.-M. Chin. Chem. Lett. 2015, 26, 977.

    Article  CAS  Google Scholar 

  42. Mai, W.-P.; Wang, J.-T.; Xiao, Y.-M.; Mao, P.; Lu, K. Tetrahedron 2015, 71, 8041.

    Article  CAS  Google Scholar 

  43. Mai, W.-P.; Sun, G.-C.; Wang, J.-T.; Song, G.; Mao, P.; Yang, L.-R.; Yuan, J.-W.; Xiao, Y.-M.; Qu, L.-B. J. Org. Chem. 2014, 79, 8094.

    Article  CAS  Google Scholar 

  44. Yang, H.; Guo, L.-N.; Duan, X.-H. RSC. Adv. 2014, 4, 52986.

    Article  CAS  Google Scholar 

  45. Bergonzini, G.; Cassani, C.; Wallentin, C.-J. Angew. Chem., Int. Ed. 2015, 54, 14066.

    Article  CAS  Google Scholar 

  46. Zheng, L.; Huang, H.; Yang, C.; Xia, W. Org. Lett. 2015, 17, 1034.

    Article  CAS  Google Scholar 

  47. Gu, Z.; Zhang, H.; Xu, P.; Cheng, Y.; Zhu, C. Adv. Synth. Catal. 2015, 357, 3057.

    Article  CAS  Google Scholar 

  48. Xia, X.-F.; Zhu, S.-L.; Li, Y.; Wang, H. RSC Adv. 2016, 6, 51703.

    Article  CAS  Google Scholar 

  49. Mai, W.-P.; Wang, J.-T.; Yang, L.-R.; Yuan, J.-W.; Xiao, Y.-M.; Mao, P.; Qu, L.-B. Org. Lett. 2014, 16, 204.

    Article  CAS  Google Scholar 

  50. Wang, H.; Guo, L.-N.; Duan, X.-H. J. Org. Chem. 2016, 81, 860.

    Article  CAS  Google Scholar 

  51. Zhao, Y.; Li, Z.; Sharma, U. K.; Sharma, N.; Song, G.; Van der Eycken, E. V. Chem. Commun. 2016, 52, 6395.

    Article  CAS  Google Scholar 

  52. Zhou, S.-L.; Guo, L.-N.; Wang, S.; Duan, X.-H. Chem. Commun. 2014, 50, 3589.

    Article  CAS  Google Scholar 

  53. Chan, C.-W.; Lee, P.-Y.; Yu, W.-Y. Tetrahedron Lett. 2015, 56, 2559.

    Article  CAS  Google Scholar 

  54. Li, X.; Xu, J.; Gao, Y.; Fang, H.; Tang, G.; Zhao, Y. J. Org. Chem. 2015, 80, 2621.

    Article  CAS  Google Scholar 

  55. Wang, Q.; Han, G.; Liu, Y.; Wang, Q. Adv. Synth. Catal. 2015, 357, 2464.

    Article  CAS  Google Scholar 

  56. Gao, F.; Yang, C.; Gao, G.-L.; Zheng, L.; Xia, W. Org. Lett. 2015, 17, 3478.

    Article  CAS  Google Scholar 

  57. Wang, H.; Sun, B.; Yang, J.; Wang, J.; Mao, P.; Yang, L.; Mai, W. J. Chem. Res. 2014, 38, 542.

    Article  CAS  Google Scholar 

  58. Wu, T.; Mu, X.; Liu, G. Angew. Chem., Int. Ed. 2011, 50, 12578.

    Article  CAS  Google Scholar 

  59. Zhang, H.; Gu, Z.; Li, Z.; Pan, C.; Li, W.; Hu, H.; Zhu, C. J. Org. Chem. 2016, 81, 2122.

    Article  CAS  Google Scholar 

  60. Wang, F.-X.; Tian, S.-K. J. Org. Chem. 2015, 80, 12697.

    Article  CAS  Google Scholar 

  61. Wang, C. H.; Alluri, S.; Nikogosyan, G.; Decarlo, C.; Monteiro, C.; Mabagos, G.; Feng, H. H.; White, A. R.; Bartolini, M.; Andrisano, V.; Zhang, L. K.; Ganguly, A. K. Tetrahedron Lett. 2016, 57, 3046.

    Article  CAS  Google Scholar 

  62. Ziegler, E.; Wimmer, T. Monatsh. Chem. 1965, 96, 1252.

    Article  CAS  Google Scholar 

  63. Liu, X.; Zhang, Q.; Zhang, D.; Xin, X.; Zhang, R.; Zhou, F.; Dong, D. Org. Lett. 2013, 15, 776.

    Article  CAS  Google Scholar 

  64. Schaus, S. E.; Hansen, U.; Bishop, H. A. WO Patent 2013052465.

  65. Akritopoulou-Zanze, I.; Whitehead, A.; Waters, J. E.; Henry, R. F.; Djuric, S. W. Tetrahedron Lett. 2007, 48, 3549.

    Article  CAS  Google Scholar 

  66. Knunyants, I. L.; Gambaryan, N. P. Russ. Chem. Bull. 1957, 6, 855. [Izv. Akad. Nauk SSSR, Ser. Khim. 1957, (7), 834.]

  67. Hazai, L.; Deák, G.; Sohár, P.; Tóth, G.; Tamás, J. J. Heterocycl. Chem. 1991, 28, 919.

    Article  CAS  Google Scholar 

  68. Bird, P. G.; Irwin, W. J. J. Chem. Soc., Perkin Trans. 1 1973, 2664.

  69. Kano, S.; Ebata, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1980, 2105.

  70. Mandal, P. K.; Cabell, L. A.; McMurray, J. S. Tetrahedron Lett. 2005, 46, 3715.

    Article  CAS  Google Scholar 

  71. Delcros, J.-G.; Tomasi, S.; Duhieu, S.; Foucault, M.; Martin, B.; Le Roch, M.; Eifler-Lima, V.; Renault, J.; Uriac, P. J. Med. Chem. 2006, 49, 232.

    Article  CAS  Google Scholar 

  72. Azarifar, D.; Sheikh, D. Synth. Commun. 2013, 43, 2517.

    Article  CAS  Google Scholar 

  73. Kozlov, N. G.; Basalaeva, L. I. Russ. J. Org. Chem. 2006, 42, 509.

    Article  CAS  Google Scholar 

  74. Kozlov, N. G.; Basalayeva, L. I.; Tychinskaya, L. Yu. Russ. J. Org. Chem. 2002, 38, 1166.

    Article  CAS  Google Scholar 

  75. Wang, X.-M.; Ye, H.-L.; Qaun, Z.-J.; Wang, X.-C. Res. Chem. Intermed. 2013, 39, 2357.

    Article  CAS  Google Scholar 

  76. Wang, X.; Wang, X.; Quan, Z.; Zhang, Z. CN Patent 102260211; Chem. Abstr. 2012, 56, 35005.

  77. Zhu, X.-T.; Li, Q.-Y.; Jiang, B.; Tu, S.-J. Heterocycles 2012, 85, 1615.

    Article  CAS  Google Scholar 

  78. Peng, J.; Jia, R.; Xu, Y.; Tu, S.; Ma, N.; Zhang, G. Chin. J. Chem. 2009, 27, 2392.

    Article  CAS  Google Scholar 

  79. Peng, J.; Hao, W.; Wang, X.; Tu, S.; Ma, N.; Zhang, G. Chin. J. Chem. 2009, 27, 1707.

    Article  CAS  Google Scholar 

  80. Wang, X.-S.; Zhang, M.-M.; Zeng, Z.-S.; Shi, D.-Q.; Tu, S.-J.; Wei, X.-Y.; Zong, Z.-M. Tetrahedron Lett. 2005, 46, 7169.

    Article  CAS  Google Scholar 

  81. Kozlov, S. N.; Basalaeva, L. I.; Ol'khovik, V. K.; Kalechits, G. V.; Matveenko, Yu. V. Russ. J. Gen. Chem. 2003, 73, 1434. [Zh. Obshch. Khim. 2003, 73, 1518.]

  82. Strods, J.; Lielbriedis, I.; Neilands, O. Latv. PSR Zinat. Akad. Vestis, Kim. Ser. 1978, (2), 225.

  83. Strods, Ya. A.; Tsiekure, V. P.; Kampars, V. E.; Lielbriedis, I. E.; Neiland, O. Ya. Chem. Heterocycl. Compd. 1978, 14, 1113. [Khim. Geterotsikl. Soedin. 1978, 1369.]

  84. Wang, X.-S.; Zhang, M.-M.; Zeng, Z.-S.; Shi, D.-Q.; Tu, S.-J.; Wei, X.-Y.; Zong, Z.-M. J. Heterocycl. Chem. 2007, 44, 441.

    Article  CAS  Google Scholar 

  85. Hao, W.-J.; Jiang, B.; Tu, S.-J.; Wu, S.-S.; Han, Z.-G.; Cao, X.-D.; Zhang, X.-H.; Yan, S.; Shi, F. J. Comb. Chem. 2009, 11, 310.

    Article  CAS  Google Scholar 

  86. Staskun, B. J. Org. Chem. 1979, 44, 875.

    Article  CAS  Google Scholar 

  87. Staskun, B. J. Org. Chem. 1980, 45, 2482.

    Article  CAS  Google Scholar 

  88. Marais, J. L. C.; Staskun, B. J. Org. Chem. 1985, 50, 4652.

    Article  CAS  Google Scholar 

  89. He, J.-Q.; Chen, C.; Yu, W.-B.; Liu, R.-R.; Xu, M.; Li, Y.-J.; Gao, J.-R.; Jia, Y.-X. Tetrahedron Lett. 2014, 55, 2805.

    Article  CAS  Google Scholar 

  90. Butke, G. P.; Jimenz, M. F.; Michalik, J.; Gorski, R. A.; Rossi, N. F.; Wemple, J. J. Org. Chem. 1978, 43, 954.

    Article  CAS  Google Scholar 

  91. Kobayashi, Y.; Li, S.; Takemoto, Y. Asian J. Org. Chem. 2014, 3, 403.

    Article  CAS  Google Scholar 

  92. Nisole, C.; Uriac, P.; Huet, J. Tetrahedron 1992, 48, 1081.

    Article  CAS  Google Scholar 

  93. Han, G.; Wang, Q.; Liu, Y.; Wang, Q. Org. Lett. 2014, 16, 5914.

    Article  CAS  Google Scholar 

  94. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.

    Article  CAS  Google Scholar 

  95. Sun, W.-W.; Cao, P.; Mei, R.-Q.; Li, Y.; Ma, Y.-L.; Wu, B. Org. Lett. 2014, 16, 480.

    Article  CAS  Google Scholar 

  96. Zhang, S.-J.; Sun, W.-W.; Cao, P.; Dong, X.-P.; Liu, J.-K.; Wu, B. J. Org. Chem. 2016, 81, 956.

    Article  CAS  Google Scholar 

  97. Wang, J.; Discordia, R. P.; Crispino, G. A.; Li, J.; Grosso, J. A.; Polniaszek, R.; Truc, V. C. Tetrahedron Lett. 2003, 44, 4271.

    Article  CAS  Google Scholar 

  98. Walser, A.; Szente, A.; Hellerbach, J. J. Org. Chem. 1973, 38, 449.

    Article  CAS  Google Scholar 

  99. Ueki, H.; Ellis, T. K.; Khan, M. A.; Soloshonok, V. A. Tetrahedron 2003, 59, 7301.

    Article  CAS  Google Scholar 

  100. Hewawasam, P.; Fan, W.; Ding, M.; Flint, K.; Cook, D.; Goggins, G. D.; Myers, R. A.; Gribkoff, V. K.; Boissard, C. G.; Dworetzky, S. I.; Starret, J. E., Jr.; Lodge, N. J. J. Med. Chem. 2003, 46, 2819.

    Article  CAS  Google Scholar 

  101. Li, X.; Huo, X.; Li, J.; She, X.; Pan, X. Chinese J. Chem. 2009, 27, 1379.

    Article  CAS  Google Scholar 

  102. Zhao, S.; He, Y.; Wu, D.; Guan, Z. J. Fluorine Chem. 2010, 131, 597.

    Article  CAS  Google Scholar 

  103. Li, B.; Park, Y.; Chang, S. J. Am. Chem. Soc. 2014, 136, 1125.

    Article  CAS  Google Scholar 

  104. Ferrer, P.; Avendano, C.; Söllhuber, M. Tetrahedron 1997, 53, 3231.

    Article  CAS  Google Scholar 

  105. Kim, Y.; Shin, E.; Beak, P.; Park, Y. S. Synthesis 2006, 22, 3805.

    Google Scholar 

  106. Ko, Y. K.; Im, C.; Do, J.; Park, Y. S. Eur. J. Org. Chem. 2014, 3460.

  107. Paquin, J.-F.; Stephenson, C. R. J.; Defieber, C.; Carreira, E. M. Org. Lett. 2005, 7, 3821.

    Article  CAS  Google Scholar 

  108. Shang, R.; Huang, Z.; Chu, L.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 4240.

    Article  CAS  Google Scholar 

  109. Taylor, J. G.; Correia, C. R. D. J. Org. Chem. 2011, 76, 857.

    Article  CAS  Google Scholar 

  110. Simonetti, S. O.; Larghi, E. L.; Kaufman, T. S. Org. Biomol. Chem. 2016, 14, 2625.

    Article  CAS  Google Scholar 

  111. Tu, S.; Zhang, J.; Jia, R.; Jiang, B.; Zhang, Y.; Jiang, H. Org. Biomol. Chem. 2007, 5, 1450.

    Article  CAS  Google Scholar 

  112. Feng, B.-B.; Xu, J.; Zhang, M.-M.; Wang, X.-S. Synthesis 2016, 48, 65.

    Article  Google Scholar 

  113. Horn, J.; Li, H. Y.; Marsden, S. P.; Nelson, A.; Shearer, R. J.; Campbell, A. J.; House, D.; Weingarten, G. G. Tetrahedron 2009, 65, 9002.

    Article  CAS  Google Scholar 

  114. Linsenmeier, A. M.; Braje, W. M. Tetrahedron 2015, 71, 6913.

    Article  CAS  Google Scholar 

  115. Li, H. Y.; Horn, J.; Campbell, A.; House, D.; Nelson, A.; Marsden, S. P. Chem. Commun. 2014, 50, 10222.

    Article  CAS  Google Scholar 

  116. Park, J. O.; Youn, S. W. Org. Lett. 2010, 12, 2258.

    Article  CAS  Google Scholar 

  117. Zhang, L.; Qureshi, Z.; Sonaglia, L.; Lautens, M. Angew. Chem., Int. Ed. 2014, 53, 13850.

    Article  CAS  Google Scholar 

  118. Ye, F.; Alper, H. Adv. Synth. Catal. 2006, 348, 1855.

    Article  CAS  Google Scholar 

  119. Dong, C.; Alper, H. Tetrahedron: Asymmetry 2004, 15, 35.

    Article  CAS  Google Scholar 

  120. Stephenson, E. F. M. J. Chem. Soc. 1956, 2557.

  121. Chen, G.; Shigenari, T.; Jain, P.; Zhang, Z.; Jin, Z.; He, J.; Li, S.; Mapelli, C.; Miller, M. M.; Poss, M. A.; Scola, P. M.; Yeung, K.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137, 3338.

    Article  CAS  Google Scholar 

  122. Birch A. M.; Kemmitt, P. D.; Martin, N. G.; Ward, R. A. WO Patent 2005123685.

  123. Koltunov, K. Yu.; Surya Prakash, G. K.; Rasul, G.; Olah, G. A. Heterocycles 2004, 62, 757.

    Article  CAS  Google Scholar 

  124. Hoshikawa, T.; Inaoue, M. Chem. Sci. 2013, 4, 3118.

    Article  CAS  Google Scholar 

  125. McDevitt, P.; Vittimberga, B. M. J. Heterocycl. Chem. 1990, 27, 1903.

    Article  CAS  Google Scholar 

  126. Caronna, T.; Morrocchi, S.; Vittimberga, B. M. J. Org. Chem. 1981, 46, 34.

    Article  CAS  Google Scholar 

  127. Pita, M.; Kdzia, J.; Janecka, A.; Pomorska, D. K.; Rozalski, M.; Krajewska, U.; Janecki, T. RSC Adv. 2015, 5, 78324.

    Article  CAS  Google Scholar 

  128. Asahara, M.; Nagamatsu, M.; Tohda, Y.; Nishiwaki, N.; Ariga, M. J. Heterocycl. Chem. 2004, 41, 803.

    Article  CAS  Google Scholar 

  129. Papillon, J. P. N.; Adams, C. M.; Hu, Q.-Y.; Lou, C.; Singh, A. K.; Zhang, C.; Carvalho, J.; Rajan, S.; Amaral, A.; Beil, M. E.; Fu, F.; Gangl, E.; Hu, C.-W.; Jeng, A. Y.; LaSala, D.; Liang, G.; Logman, M.; Maniara, W. M.; Rigel, D. F.; Smith, S. A.; Ksander, G. M. J. Med. Chem. 2015, 58, 4749.

    Article  CAS  Google Scholar 

  130. Hu, Q.; Ksander, G. M. WO Patent 2008076860.

  131. Miki, T.; Kori, M.; Fujishima, A.; Mabuchi, H.; Tozawa, R.; Nakamura, M.; Sugiyama, Y.; Yukimasa, H. Bioorg. Med. Chem. 2002, 10, 385.

    Article  CAS  Google Scholar 

  132. Black, R. M. US Patent 4048177.

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  1. Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena St., Riga, LV, 1048, Latvia

    Inese Mieriņa, Māra Jure & Agnese Stikute

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  1. Inese Mieriņa
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  2. Māra Jure
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 509–523

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Mieriņa, I., Jure, M. & Stikute, A. Synthetic approaches to 4-(het)aryl-3,4-dihydroquinolin-2(1H)-ones. Chem Heterocycl Comp 52, 509–523 (2016). https://doi.org/10.1007/s10593-016-1920-9

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