Synthesis 2017; 49(22): 5067-5080
DOI: 10.1055/s-0036-1590860
paper
© Georg Thieme Verlag Stuttgart · New York

The Palladium-Catalyzed Heteroarylation of Adamantylalkyl Amines with Dihalogenopyridines: Scope and Limitations

Anton S. Abela, Alexei D. Averina, b, Alexei K. Buryakb, Evgenii N. Savelyevc, Boris S. Orlinsonc, Ivan A. Novakovc, Irina P. Beletskaya*a, b
  • aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1–3, Moscow 119991, Russian Federation
  • bA. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 31-4 Leninskii pr., Moscow 119991, Russian Federation
  • cVolgograd State Technical University, 28 pr. Lenina, Volgograd 400005, Russian Federation   Email: alexaveron@yandex.ru
This work was financially supported by the Russian Foundation for Basic Research grants 13-03-00572 and 16-03-00349.
Further Information

Publication History

Received: 15 June 2017

Accepted after revision: 12 July 2017

Publication Date:
07 August 2017 (eFirst)

Abstract

Palladium-catalyzed heteroarylation of adamantylalkyl amines characterized by different steric hindrances at the amino group was carried out using 2,3-, 2,5-, 2,6-, and 3,5-dihalogenopyridines. The dependence of the results of the coupling on the nature of the halogen atoms (bromine, chlorine), their position in the pyridine ring, and on the structure of adamantylalkyl amines was investigated. The application of dichloropyridines or bromochloropyridines was shown to be advantageous over the use dibromopyridines in many cases. Selective substitution of bromine atom in positions 3 and 5 in the presence of chlorine atom in position 2 of the pyridine ring was observed. The possibility of N,N-diheteroarylation of adamantane-containing amines with 2,5-dihalogenopyridines was shown, and diamination of 2,6- and 3,5-dihalogenopyridines was demonstrated.

Supporting Information

 
  • References

  • 1 Wanka L. Iqbal K. Schreiner PR. Chem. Rev. 2013; 113: 3516
  • 2 Liu J. Obando D. Liao V. Lifa T. Codd R. Eur. J. Med. Chem. 2011; 46: 1949
  • 3 Gilligan BS. Veale J. Wodak J. Med. J. Aust. 1970; 2: 634
  • 4 Dolin, R.; Bentley, D. W. In Proceedings of the Viratek-UCLA Symposium, Keystone, CO (USA), April 20–25, 1985, 317.
  • 5 Svenson TN. Eur. J. Pharmacol. 1973; 34: 232
  • 6 Morozov IS. Petrov VI. Sergeeva SA. Farmakologiya adamantanov [Pharmacology of Adamantanes] (in Russian) . Volgodrad. Med. Acad; Volgograd; 2001: 189
  • 7 Avdyunina NI. Morozov IS. Bol’shakova RF. Militareva NA. Klimova NV. Bykov NP. Pyatin BM. Khranilov AA. Dvalishvili ÉG. Pharm. Chem. J. (Engl. Transl.) 1988; 22: 543
  • 8 Da Settimo A. Marini AM. Primofiore G. da Settimo F. Farmacology 1995; 50: 321
  • 9 Ficarra R. Ficarra P. Tommasini A. Fenech G. Pizzementi FC. Bisignano G. Boll. Chim. Farm. 1984; 123: 317
  • 10 Baxter A. Bent J. Bowers K. Braddock M. Brough S. Fagura M. Lawson M. Mclnally T. Mortimore M. Robertson M. Weaver R. Webborn P. Bioorg. Med. Chem. Lett. 2003; 13: 4047
  • 11 Balzarini J. Orzeszko-Krzesińska B. Maurin JK. Orzeszko A. Eur. J. Med. Chem. 2009; 44: 303
  • 12 Danilenko GI. Rybalko SL. Maksimov YN. Baklan VF. Guzhova SV. Pharm. Chem. J. 2000; 34: 23
  • 13 Mibu N. Yokomizo K. Miyata T. Sumoto K. Chem. Pharm. Bull. 2007; 55: 1406
  • 14 Rohde JJ. Pliushchev MA. Sorensen BK. Wodka D. Shuai Q. Wang J. Fung S. Monzon KM. Chiou WJ. Pan L. Deng X. Chovan LE. Ramaiya A. Mullally M. Henry RF. Stolarik DF. Imade HM. Marsh KC. Beno DW. A. Fey TA. Droz BA. Brune ME. Camp HS. Sham HL. Frevert EU. Jacobson PB. Link JT. J. Med. Chem. 2007; 50: 149
  • 15 Ryu JH. Kim S. Han HY. Son HJ. Lee HJ. Shin YA. Kim J.-S. Park H.-G. Bioorg. Med. Chem. Lett. 2015; 25: 695
  • 16 Sorensen B. Rohde J. Wang J. Fung S. Monzon K. Chiou W. Pan L. Deng X. Stolarik D. Frevert EU. Jacobson P. Link JT. Bioorg. Med. Chem. Lett. 2006; 16: 5958
  • 17 Harikishore A. Leow ML. Niang M. Rajan S. Pasunooti KK. Preiser PR. Liu X. Yoon HS. ACS Med. Chem. Lett. 2013; 4: 1097
  • 18 Leovac VM. Rodić MV. Jovanović LS. Joksović MD. Stanojković T. Vujčić M. Sladić D. Marković V. Vojinović-Ješić LS. Eur. J. Inorg. Chem. 2015; 882
  • 19 Collins KC. Janda KD. Bioconjugate Chem. 2014; 25: 593
  • 20 Levina MN. Bull. Exp. Biol. Med. (Engl. Transl.) 2005; 139: 337
  • 21 Wagaw S. Buchwald SL. J. Org. Chem. 1996; 61: 7240
  • 22 Sun X. Yu Z. Wu S. Wen J. Organometallics 2005; 24: 2959
  • 23 Suzuki Y. Yanagi T. Kanbara T. Yamamoto T. Synlett 2005; 263
  • 24 Wang M.-X. Zhang X.-H. Zheng Q.-Y. Angew. Chem. Int. Ed. 2004; 43: 838
  • 25 Subat M. Konig B. Synthesis 2001; 1818
  • 26 Desmarets T. Schneider R. Fort Y. Tetrahedron Lett. 2000; 41: 2875
  • 27 Jonckers TH. M. Maes BU. W. Lemière GL. F. Dommisse R. Tetrahedron 2001; 57: 7027
  • 28 Koley M. Wimmer L. Schnürch M. Mihovilovic MD. Eur J. Org. Chem. 2011; 1972
  • 29 Ji J. Li T. Bunnelle VH. Org. Lett. 2003; 5: 4611
  • 30 Hostyn S. Van Baelen G. Lemière GL. F. Maes BU. W. Adv. Synth. Catal. 2008; 350: 2653
  • 31 Beletskaya IP. Averin AD. Pleshkova NA. Borisenko AA. Serebryakova MV. Denat F. Guilard R. Synlett 2005; 87
  • 32 Beletskaya IP. Averin AD. Ulanovskaya OA. Fedotenko IA. Borisenko AA. Serebryakova MV. Denat F. Guilard R. Chem. Lett. 2005; 34: 1100
  • 33 Averin AD. Ulanovskaya OA. Fedotenko IA. Borisenko AA. Serebryakova MV. Beletskaya IP. Helv. Chim. Acta 2005; 88: 1983
  • 34 Averin AD. Ulanovskaya OA. Borisenko AA. Serebryakova MV. Beletskaya IP. Tetrahedron Lett. 2006; 47: 2691
  • 35 Averin AD. Ulanovskaya OA. Pleshkova NA. Borisenko AA. Beletskaya IP. Collect. Czech. Chem. Commun. 2007; 72: 785
  • 36 Averin AD. Ranyuk ER. Golub SL. Buryak AK. Savelyev EN. Orlinson BS. Novakov IA. Beletskaya IP. Synthesis 2007; 2215
  • 37 Averin AD. Baranova TYu. Abel AS. Kovalev VV. Buryak AK. Butov GM. Savelyev EN. Orlinson BS. Novakov IA. Beletskaya IP. Russ. J. Org. Chem. 2013; 49 1
  • 38 Abel AS. Averin AD. Anokhin MV. Maloshitskaya OA. Butov GM. Savelyev EN. Orlinson BS. Novakov IA. Beletskaya IP. Russ. J. Org. Chem. 2015; 51: 301
  • 39 Averin AD. Shukhaev AV. Golub SL. Buryak AK. Beletskaya IP. Synthesis 2007; 2995
  • 40 Gopalan B. Thomas A. Shah DM. Patent PCT Int. Appl. WO 2006090244, 2006
  • 41 Gerzon K. Krumkalns EV. Brindle RL. Marshall FJ. Root MA. J. Med. Chem. 1963; 6: 760
  • 42 Ukai T. Kawazura H. Ishii Y. Bonnet JJ. Ibers JA. J. Organomet. Chem. 1974; 65: 253