Synthesis 2018; 50(02): 193-210
DOI: 10.1055/s-0036-1589520
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Direct C–H Functionalization of Pyrimidines

a  Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy St. 22, Ekaterinburg 620 990, Russian Federation
b  Ural Federal University, Mira St. 19, Ekaterinburg 620 002, Russian Federation   Email: Verbitsky@ios.uran.ru
,
Gennady L. Rusinov
a  Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy St. 22, Ekaterinburg 620 990, Russian Federation
b  Ural Federal University, Mira St. 19, Ekaterinburg 620 002, Russian Federation   Email: Verbitsky@ios.uran.ru
,
Oleg N. Chupakhin
a  Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy St. 22, Ekaterinburg 620 990, Russian Federation
b  Ural Federal University, Mira St. 19, Ekaterinburg 620 002, Russian Federation   Email: Verbitsky@ios.uran.ru
,
Valery N. Charushin
a  Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy St. 22, Ekaterinburg 620 990, Russian Federation
b  Ural Federal University, Mira St. 19, Ekaterinburg 620 002, Russian Federation   Email: Verbitsky@ios.uran.ru
› Author Affiliations
The research was financially supported by the Russian Science Foundation (Project No. 15-13-00077).
Further Information

Publication History

Received: 24 August 2017

Accepted after revision: 15 September 2017

Publication Date:
14 December 2017 (online)


Abstract

Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.

1 Introduction

2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives

3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives

4 Deprotonative Metalation of Pyrimidine Derivatives

5 Conclusions

 
  • References

  • 1 Rewcastle GW. In Comprehensive Heterocyclic Chemistry III . Vol. 8. Katritzky AR. Ramsden CA. Scriven EF. V. Taylor RJ. K. Chap. 2 Elsevier; Amsterdam: 2008: 117-272
  • 2 Pozharskii AF. Sodatenkov AT. Katritzky AR. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications. Wiley; Chichester: 2011. 2nd ed.
  • 3 Itami K. Yamazaki D. Yoshida J.-I. J. Am. Chem. Soc. 2004; 126: 15396
  • 4 Achelle S. Plé N. Curr. Org. Synth. 2012; 9: 163
  • 5 Achelle S. Baudequin C. In Targets in Heterocyclic Systems Spinelli D.; Royal Society of Chemistry: Cambridge , 2013; Vol. 17: 1-34
  • 6 Hill MD. Movassaghi M. Chem. Eur. J. 2008; 14: 6836
  • 7 Radi M. Schenone S. Botta M. Org. Biomol. Chem. 2009; 7: 2841
  • 8 Gore RP. Rajput AP. Drug Invention Today 2013; 5: 148
  • 9 Shamsuzzaman, Dar AM. Eur. Chem. Bull. 2015; 4: 249
  • 10 Mahfoudh M. Abderrahim R. Leclerc E. Campagne J.-M. Eur. J. Org. Chem. 2017; 2856
  • 11 Schomaker JM. Delia TJ. J. Org. Chem. 2001; 66: 7125
  • 12 Molander GA. Katona BW. Machrouhi F. J. Org. Chem. 2002; 67: 8416
  • 13 Qing F.-L. Wang R. Li B. Zheng X. Meng W.-D. J. Fluorine Chem. 2003; 120: 21
  • 14 Guram AS. King AO. Allen JG. Wang X. Schenkel LB. Chan J. Bunel EE. Faul MM. Larsen RD. Martinelli MJ. Reider PJ. Org. Lett. 2006; 8: 1787
  • 15 Ceide SC. Montalban AG. Tetrahedron Lett. 2006; 47: 4415
  • 16 Delia TJ. Schomaker JM. Kalinda AS. J. Heterocycl. Chem. 2006; 43: 127
  • 17 Large JM. Clarke M. Williamson DM. McDonald E. Collins I. Synlett 2006; 861
  • 18 Hartung CG. Backes AC. Felber B. Missioy A. Philipp A. Tetrahedron 2006; 62: 10055
  • 19 Colombo M. Giglio M. Peretto I. J. Heterocycl. Chem. 2008; 45: 1077
  • 20 Zhou Y. Xi Z. Chen W. Wang D. Organometallics 2008; 27: 5911
  • 21 Achelle S. Ramondenc Y. Marsais F. Plé N. Eur. J. Org. Chem. 2008; 3129
  • 22 Fleckenstein CA. Plenio H. J. Org. Chem. 2008; 73: 3236
  • 23 Lee D.-H. Choi M. Yu B.-W. Ryoo R. Taher A. Hossain S. Jin M.-J. Adv. Synth. Catal. 2009; 351: 2912
  • 24 Tumkevicius S. Dodonova J. Baskirova I. Voitechovicius A. J. Heterocycl. Chem. 2009; 46: 960
  • 25 Lee D.-H. Jung J.-Y. Jin M.-J. Green Chem. 2010; 12: 2024
  • 26 Błachut D. Szawkało J. Czarnocki Z. Synthesis 2011; 3496
  • 27 Farahat AA. Boykin DW. Synthesis 2012; 44: 120
  • 28 Isley NA. Gallou F. Lipshutz BH. J. Am. Chem. Soc. 2013; 135: 17707
  • 29 Achelle S. Rodriguez-Lopez J. Robin-le Guen F. J. Org. Chem. 2014; 79: 7564
  • 30 Skardziute L. Dodonova J. Voitechovicius A. Jovaisaite J. Komskis R. Voitechoviciute A. Bucevicius J. Kazlauskas K. Jursenasa S. Tumkevicius S. Dyes Pigm. 2015; 118: 118
  • 31 Rodríguez-Aguilar J. Ordóñez B. Vidal M. Rezende MC. Domínguez M. SynOpen 2017; 1: 24
  • 32 Olivera R. Pascual S. Herrero M. San Martin R. Domínguez E. Tetrahedron Lett. 1998; 39: 7155
  • 33 Gazivoda T. Kristafor S. Cetina M. Nagl A. Raic-Malic S. Struct. Chem. 2008; 19: 441
  • 34 Stanetty P. Hattinger G. Schnuerch M. Mihovilovic MD. J. Org. Chem. 2005; 70: 5215
  • 35 Stanetty P. Roehrling J. Schnuerch M. Mihovilovic MD. Tetrahedron 2006; 62: 2380
  • 36 Edo K. Yamanaka H. Sakamoto T. Heterocycles 1978; 9: 271
  • 37 Kim CS. Russell KC. J. Org. Chem. 1998; 63: 8229
  • 38 Hocková D. Holy A. Masojídková M. Votruba I. Tetrahedron 2004; 60: 4983
  • 39 Berg TC. Bakken V. Gundersen LL. Petersen D. Tetrahedron 2006; 62: 6121
  • 40 Benderitter P. de Araújo-Júnior JX. Schmitt M. Bourguignon J.-J. Tetrahedron 2007; 63: 12465
  • 41 Fürstner A. Letner A. Méndez M. Krause H. J. Am. Chem. Soc. 2002; 124: 13856
  • 42 Boully L. Darabantu M. Turck A. Plé N. J. Heterocycl. Chem. 2005; 42: 1423
  • 43 Wimmer L. Rycek L. Koley M. Schnürch M. Top. Heterocycl. Chem. 2016; 45: 61
  • 44 Gayakhe V. Sanghvi YS. Fairlamb IJ. S. Kapdi AR. Chem. Commun. 2015; 51: 11944
  • 45 Rossi R. Lessia M. Manzinia C. Marianettic G. Bellina F. Synthesis 2016; 48: 3821
  • 46 Besson T. Fruit C. Synthesis 2016; 48: 3879
  • 47 Rossi R. Lessi M. Manzini C. Marianetti G. Bellina F. Tetrahedron 2016; 72: 1795
  • 48 Yang Y. Lan J. You J. Chem. Rev. 2017; 117: 8787
  • 49 Murakami K. Yamada S. Kaneda T. Itami K. Chem. Rev. 2017; 117: 9302
  • 50 Chupakhin ON. Charushin VN. van der Plas HC. Nucleophilic Aromatic Substitution of Hydrogen . Academic Press; New York: 1994: 367
  • 51 Charushin VN. Chupakhin ON. Pure Appl. Chem. 2004; 76: 1621
  • 52 Charushin VN. Chupakhin ON. Mendeleev Commun. 2007; 17: 249
  • 53 Makosza M. Wojciechowski K. Chem. Rev. 2004; 104: 2631
  • 54 Makosza M. Chem. Soc. Rev. 2010; 39: 2855
  • 55 Charushin VN. Chupakhin ON. Metal Free C–H Functionalization of Aromatics. Nucleophilic Displacement of Hydrogen. In Topics in Heterocyclic Chemistry. Vol. 37. Charushin VN. Chupakhin ON. Springer; Heidelberg: 2014
  • 56 Chupakhin ON. Charushin VN. Tetrahedron Lett. 2016; 57: 2665
  • 57 Liu B. Huang Y. Lan J. Song F. You J. Chem. Sci. 2013; 4: 2163
  • 58 Yu Y.-Y. Georg GI. Chem. Commun. 2013; 49: 3694
  • 59 Kim KH. Lee HS. Kim JN. Tetrahedron Lett. 2011; 52: 6228 ; and references therein
  • 60 Kianmehr E. Rezaeefard M. Khalkhalia MR. Khan KM. RSC Adv. 2014; 4: 13764
  • 61 Čerňová M. Pohl R. Hocek M. Eur. J. Org. Chem. 2009; 3698
  • 62 Čerňová M. Čerňa I. Pohl R. Hocek M. J. Org. Chem. 2011; 76: 5309
  • 63 Nagib A. MacMillan DW. C. Nature (London) 2011; 480: 224
  • 64 Ji Y. Brueckl T. Baxter RD. Fujiwara Y. Seiple IB. Su S. Blackmond DG. Baran PS. Proc. Natl. Acad. Sci. U.S.A. 2011; 108: 14411
  • 65 Čerňová M. Pohl R. Klepetářová B. Hocek M. Heterocycles 2014; 89: 1159
  • 66 Shimizu M. Hayama N. Kimachi T. Inamoto K. Synthesis 2017; 49: 4183
  • 67 Laclef S. Harari M. Godeau J. Schmitz-Afonso I. Bischoff L. Hoarau C. Levacher V. Fruit C. Besson T. Org. Lett. 2015; 17: 1700
  • 68 Godeau J. Harari M. Laclef S. Deau E. Fruit C. Besson T. Eur. J. Org. Chem. 2015; 7705
  • 69 Minisci F. Bernardi R. Bertini F. Galli R. Perchinummo M. Tetrahedron 1971; 27: 3575
  • 70 Minisci F. Vismara E. Fontana F. Morini G. Serravalle M. Giordano C. J. Org. Chem. 1987; 52: 730
  • 71 Minisci F. Vismara E. Fontana F. Heterocycles 1989; 28: 489
  • 72 Giordano C. Minisci F. Tortelli V. Vismara E. J. Chem. Soc., Perkin Trans. 2 1984; 293
  • 73 Kanomata N. Igarashi M. Tada M. Heterocycles 1993; 36: 1127
  • 74 Togo H. Ishigami S. Fujii M. Ikuma T. Yokohama M. J. Chem. Soc., Perkin Trans. 1 1994; 2931
  • 75 Sakamoto T. Konno S. Yamanaka H. Heterocycles 1977; 6: 1616
  • 76 Murthy KS. K. Knaus EE. Drug Dev. Res. 1999; 46: 155
  • 77 Shore DG. M. Wasik KA. Lyssikatos JP. Estrada AA. Tetrahedron Lett. 2015; 56: 4063
  • 78 Mai W.-P. Sun B. You L.-Q. Yang L.-R. Mao P. Yuan J.-W. Xiao Y.-M. Qu L.-B. Org. Biomol. Chem. 2015; 13: 2750
  • 79 Mai DN. Baxter RD. Org. Lett. 2016; 18: 3738
  • 80 Seiple IB. Su S. Rodriguez RA. Gianatassio R. Fujiwara Y. Sobel AL. Baran PS. J. Am. Chem. Soc. 2010; 132: 13194
  • 81 Tian M. Yu M. Shi T. Hu J. Li S. Xu J. Chen N. Du H. Eur. J. Org. Chem. 2017; 3415
  • 82 Wang J. Wang S. Wang G. Zhang J. Yu X.-Q. Chem. Commun. 2012; 48: 11769
  • 83 Guchhait SK. Kashyap M. Saraf S. Synthesis 2010; 1166
  • 84 Molander GA. Colombel V. Braz VA. Org. Lett. 2011; 13: 1852
  • 85 DiRocco DA. Dykstra K. Krska S. Vachal P. Conway DV. Tudge M. Angew. Chem. Int. Ed. 2014; 53: 4802
  • 86 Jin J. MacMillan DW. C. Angew. Chem. Int. Ed. 2015; 54: 1565
  • 87 Li G.-X. Morales-Rivera CA. Wang Y. Gao F. He G. Liu P. Chen G. Chem. Sci. 2016; 7: 6407
  • 88 Larsen MA. Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4287
  • 89 Scott JS. Birch AM. Brocklehurst KJ. Broo A. Brown HS. Butlin RJ. Clarke DS. Davidsson Ö. Ertan A. Goldberg K. Groombridge SD. Hudson JA. Laber D. Leach AG. MacFaul PA. McKerrecher D. Pickup A. Schofield P. Svensson PH. Sörme P. Teague J. J. Med. Chem. 2012; 55: 5361
  • 90 Bredereck H. Gompper R. Herlinger H. Angew. Chem. 1958; 70: 571
  • 91 Bredereck H. Gompper R. Herlinger H. Chem. Ber. 1958; 91: 2832
  • 92 Brown DJ. Cowden WB. Strekowski L. Aust. J. Chem. 1982; 35: 1209
  • 93 Strekowski L. Harden DB. Watson RA. Synthesis 1988; 70
  • 94 Harden DB. Mokrosz MJ. Strekowski L. J. Org. Chem. 1988; 53: 4137
  • 95 Strekowski L. Harden DB. Grubb WB. Patterson SE. Czarny A. Mokrosz MJ. Cegla MN. Wydra RL. J. Heterocycl. Chem. 1990; 27: 1393
  • 96 Smith AL. Brennan PE. Demorin FF. Liu G. Paras NA. Retz DM. WO 2006066172, 2006
  • 97 Abdou IM. J. Chem. Res. 2006; 12: 785
  • 98 Saczewski J. Paluchowska A. Klenc J. Raux E. Barnes S. Sullivan S. Duszynska B. Bojarski AJ. Strekowski L. J. Heterocycl. Chem. 2009; 46: 1259
  • 99 Alexander CW. De D. Khanna IK. Pillarisetti S. US 20100144722, 2010
  • 100 Morimoto H. Shimadzu H. Hosaka T. Kawase Y. Yasuda K. Kikkawa K. Yamfuchi-Kohno R. Yamada K. Bioorg. Med. Chem. Lett. 2002; 12: 81
  • 101 Bursavich MG. Lombardi S. Gilbert AM. Org. Lett. 2005; 7: 4113
  • 102 Pelletier JC. Lundquist JT. IV. Gilbert AM. Alon N. Bex FJ. Bhat BM. Bursavich MG. Coleburn VE. Felix LA. Green DM. Green P. Hauze DB. Kharode YP. Lam H.-S. Lockhead SR. Magolda RL. Matteo JJ. Mehlmann JF. Milligan C. Murrills RJ. Pirrello J. Selim S. Sharp MC. Unwalla RJ. Vera MD. Wrobel JE. Yaworsky P. Bodine PV. N. J. Med. Chem. 2009; 52: 6962
  • 103 Gilbert AM. Bursavich MG. Alon N. Bhat BM. Bex FJ. Cain M. Coleburn V. Gironda V. Green P. Hauze DB. Kharode Y. Krishnamurthy G. Kirisits M. Lam H.-S. Liu Y.-B. Lombardi S. Matteo J. Murrills R. Robinson JA. Selim S. Sharp M. Unwalla R. Varadarajan U. Zhao W. Yaworsky PJ. Bioorg. Med. Chem. Lett. 2010; 20: 366
  • 104 Strekowski L. Sączewski J. Raux EA. Fernando NT. Klenc J. Paranjpe S. Raszkiewicz A. Blake AL. Ehalt AJ. Barnes S. Baranowski TC. Sullivan SM. Satała G. Bojarski AJ. Molecules 2016; 21: 433
  • 105 Kovalev IS. Kopchuk DS. Zyryanov GV. Rusinov VL. Chupakhin ON. Charushin VN. Russ. Chem. Rev. 2015; 84: 1191
  • 106 Wu Y. Wu Y. Zou D. Li J. Guo R. Gao J. Qi B. Niu C. CN 103193718, 2013
  • 107 Rasputin NA. Demina NS. Irgashev RA. Rusinov GL. Chupakhin ON. Charushin VN. Tetrahedron 2017; 73: 5500
  • 108 Girke WP. K. Tetrahedron Lett. 1976; 17: 3537
  • 109 Girke WP. K. Chem. Ber. 1979; 112: 1
  • 110 Girke WP. K. Chem. Ber. 1979; 112: 1348
  • 111 Itsikson NA. Beresnev DG. Rusinov GL. Chupakhin ON. ARKIVOC 2004; (xii): 6 http://www.arkat-usa.org/home
  • 112 Bartashevich EV. Plekhanov PV. Rusinov GL. Potemkin VA. Belik AV. Chupakhin ON. Russ. Chem. Bull. 1999; 48: 1553
  • 113 Verbitskiy EV. Cheprakova EM. Slepukhin PA. Kodess MI. Ezhikova MA. Pervova MG. Rusinov GL. Chupakhin ON. Charushin VN. Tetrahedron 2012; 68: 5445
  • 114 Verbitskiy EV. Rusinov GL. Charushin VN. Chupakhin ON. Cheprakova EM. Slepukhin PA. Pervova MG. Ezhikova MA. Kodess MI. Eur. J. Org. Chem. 2012; 6612
  • 115 Verbitskiy EV. Cheprakova EM. Zhilina EF. Kodess MI. Ezhikova VA. Pervova VG. Slepukhin PA. Subbotina JO. Schepochkin AV. Rusinov GL. Chupakhin ON. Charushin VN. Tetrahedron 2013; 69: 5164
  • 116 Kravchenko MA. Verbitskiy EV. Medvinskiy ID. Rusinov GL. Charushin VN. Bioorg. Med. Chem. Lett. 2014; 24: 3118
  • 117 Cheprakova EM. Verbitskiy EV. Ezhikova MA. Kodess MI. Pervova MG. Slepukhin PA. Toporova MS. Kravchenko MA. Medvinskiy ID. Rusinov GL. Charushin VN. Russ. Chem. Bull. 2014; 63: 1350
  • 118 Verbitskiy EV. Cheprakova EM. Slepukhin PA. Kravchenko MA. Skornyakov SN. Rusinov GL. Chupakhin ON. Charushin VN. Eur. J. Med. Chem. 2015; 97: 225
  • 119 Verbitskiy EV. Baskakova SA. Kravchenko MA. Skornyakov SN. Rusinov GL. Chupakhin ON. Charushin VN. Bioorg. Med. Chem. 2016; 24: 3771
  • 120 Verbitskiy EV. Rusinov GL. Chupakhin ON. Charushin VN. ARKIVOC 2016; (iv): 204 http://www.arkat-usa.org/home
  • 121 Verbitskiy EV. Baskakova SA. Gerasimova NA. Evstigneeva NP. Zil’berberg NV. Kungurov NV. Kravchenko MA. Skornyakov SN. Pervova MG. Rusinov GL. Chupakhin ON. Charushin VN. Bioorg. Med. Chem. Lett. 2017; 27: 3003
  • 122 Verbitskiy EV. Cheprakova EM. Subbotina JO. Schepochkin AV. Slepukhin PA. Rusinov GL. Charushin VN. Chupakhin ON. Makarova NI. Metelitsa AV. Minkin VI. Dyes Pigm. 2014; 100: 201
  • 123 Verbitskiy EV. Schepochkin AV. Makarova NI. Dorogan IV. Metelitsa AV. Minkin VI. Kozyukhin SA. Emets VV. Grindberg VA. Chupakhin ON. Rusinov GL. Charushin VN. J. Fluoresc. 2015; 25: 763
  • 124 Verbitskiy EV. Baranova AA. Lugovik KI. Shafikov MZ. Khokhlov KO. Cheprakova EM. Rusinov GL. Chupakhin ON. Charushin VN. Anal. Bioanal. Chem. 2016; 408: 4093
  • 125 Verbitskiy EV. Baranova AA. Lugovik KI. Khokhlov KO. Cheprakova EM. Rusinov GL. Chupakhin ON. Charushin VN. ARKIVOC 2016; (iii): 360 ; http://www.arkat-usa.org/home
  • 126 Verbitskiy EV. Cheprakova EM. Baranova AA. Khokhlov KO. Lugovik KI. Rusinov GL. Chupakhin ON. Charushin VN. Chem. Heterocycl. Compd. 2016; 52: 904
  • 127 Verbitskiy EV. Baranova AA. Lugovik KI. Khokhlov KO. Cheprakova EM. Shafikov MZ. Rusinov GL. Chupakhin ON. Charushin VN. Dyes Pigm. 2017; 137: 360
  • 128 Baranova AA. Khokhlov KO. Chuvashov RD. Verbitskiy EV. Cheprakova EM. Rusinov GL. Charushin VN. J. Phys. Conf. Ser. 2017; 830: 012159
  • 129 Rusinov GL. Plekhanov PV. Ponomareva AU. Chupakhin ON. Mendeleev Commun. 1999; 9: 233
  • 130 Rusinov GL. Gorbunov EB. Charushin VN. Chupakhin ON. Tetrahedron Lett. 2007; 48: 5873
  • 131 Gorbunov EB. Rusinov GL. Ulomskii EN. El’tsov OS. Rusinov VL. Kartsev VG. Charushin VN. Khalymbadzha IA. Chupakhin ON. Chem. Nat. Compd. 2016; 52: 708
  • 132 Gorbunov EB. Rusinov GL. Ulomskii EN. Rusinov VL. Charushin VN. Chupakhin ON. Tetrahedron Lett. 2016; 57: 2303
  • 133 Verbitskiy EV. Gorbunov EB. Baranova AA. Lugovik KI. Khokhlov KO. Cheprakova EM. Kim GA. Rusinov GL. Chupakhin ON. Charushin VN. Tetrahedron 2016; 72: 4954
  • 135 Utepova IA. Trestsova MA. Chupakhin ON. Charushin VN. Rempel AA. Green Chem. 2015; 17: 4401
  • 136 Chupakhin ON. Shchepochkin AV. Charushin VN. Green Chem. 2017; 19: 2931
  • 137 Chupakhin ON. Charushin VN. van der Plas HC. Tetrahedron 1988; 44: 1
  • 138 Gulevskaya AV. Maes BU. W. Meyers C. Herrebout WA. van der Veken BJ. Eur. J. Org. Chem. 2006; 5305
  • 139 Verbeeck S. Herrebout WA. Gulevskaya AV. van der Veken BJ. Maes BU. W. J. Org. Chem. 2010; 75: 5126
  • 140 Yanagisawa S. Ueda K. Taniguchi T. Itami K. Org. Lett. 2008; 10: 4673
  • 141 Ambala S. Thatikonda T. Sharma S. Munagala G. Yempalla KR. Vishwakarmaa RA. Singh PP. Org. Biomol. Chem. 2015; 13: 11341
  • 142 Tang R.-J. Kang L. Yang L. Adv. Synth. Catal. 2015; 357: 2055
  • 143 Thatikonda T. Singh U. Ambala S. Vishwakarma RA. Singh PP. Org. Biomol. Chem. 2016; 14: 4312
  • 144 Turck A. Plé N. Mongin F. Quéquiner G. Tetrahedron 2001; 57: 4489
  • 145 Schlosser M. Lefebvre O. Ondi L. Eur. J. Org. Chem. 2006; 1593
  • 146 Chevallier F. Mongin F. Chem. Soc. Rev. 2008; 37: 595
  • 147 Kolarovič A. Top Heterocycl. Chem. 2013; 31: 21
  • 148 Ple N. Turck A. Couture K. Queguiner G. J. Org. Chem. 1995; 60: 3781
  • 149 Galeta J. Šála M. Dračinský M. Vrábel M. Havlas Z. Nencka R. Org. Lett. 2016; 18: 3594