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Synthesis 2017; 49(16): 3700-3709
DOI: 10.1055/s-0036-1590470
DOI: 10.1055/s-0036-1590470
paper
A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones
This work was supported by the Ministry of Education and Science of the Russian Federation (project number 4.1657.2017/4.6).Further Information
Publication History
Received: 26 February 2017
Accepted after revision: 22 April 2017
Publication Date:
07 June 2017 (online)
Abstract
A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[c][1,7]naphthyridin-4(3H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1H)-ones and aromatic aldehydes in a strong acidic media (trifluoroacetic, phosphorous or polyphosphorous acids) under heating. The initial imine derivatives undergo Pictet–Spengler condensation to form intermediate 6-aryl-5,6-dihydrobenzo[c]-1,7-naphthyridin-4(3H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1H)-ones as the final products.
Key words
naphthyridines - pyridines - Pictet–Spengler reaction - intramolecular cyclization - X-ray structural analysisSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1590470.
- Supporting Information
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References
- 1a Brown DJ. Chem. Heterocycl. Compd. 2008; 63: 1
- 1b Litvinov VP. Adv. Heterocycl. Chem. 2006; 91: 189
- 2a Shubina LK. Kalinovsky AI. Fedorov SN. Radchenko OS. Denisenko VA. Dmitrenok PS. Dyshlovoy SA. Krasokhin VB. Stonik VA. Nat. Prod. Commun. 2009; 4: 1085
- 2b Shaari K. Ling KC. Rashid ZM. Jean TP. Abas F. Raof SM. Zainal Z. Lajis NH. Mohamad H. Ali AM. Mar. Drugs 2009; 7: 1
- 2c Sandjo LP. Kuete V. Biavatti MW. J. Org. Chem. 2015; 11: 1667
- 2d Li X. Xu M. Zhao Y. Xu J. Molecules 2010; 15: 9298
- 2e Bracher F. Arch. Pharm. 1989; 322: 511
- 2f Prager RH. Were ST. Aust. J. Chem. 1983; 36: 1441
- 3a Ohizumi Y. Kajiwara A. Nakamura H. Kobayashi J. J. Pharm. Pharmacol. 1984; 36: 785
- 3b Pettit GR. Hoffmann H. Herald DL. McNulty J. Murphy A. Higgs KC. Hamel E. Lewin NE. Pearce LV. Blumberg PM. Pettit RK. Knight JC. J. Org. Chem. 2004; 69: 2251
- 3c Bowling JJ. Pennaka HK. Ivey K. Wahyuono S. Kelly M. Schinazi RF. Valeriote FA. Graves DE. Hamann MT. Chem. Biol. Drug Des. 2008; 71: 205
- 4a Karim RM. Schönbrunn E. J. Med. Chem. 2016; 59: 4459
- 4b Martin LJ. Koegl M. Bader G. Cockcroft X. Fedorov O. Fiegen D. Gerstberger T. Hofmann MH. Hohmann AF. Kessler D. Knapp S. Knesl P. Kornigg S. Müller S. Nar H. Rogers C. Rumpel K. Schaaf O. Steurer S. Tallant C. Vakoc CR. Zeeb M. Zoephel A. Pearson M. Boehmelt G. McConnell D. J. Med. Chem. 2016; 59: 4462
- 4c Liu S. Duffy BC. Quinn JF. Jiang MX. Wang R. Martin GS. Zhao H. Molino BF. Young PR. Patent US9271978 B2, 2, 2016
- 5a Hosoki R. Yanagisawa M. Onishi Y. Yoshioka K. Otsuka M. Eur. J. Pharm. 1998; 341: 235
- 5b Ban T. Doi T. Patent EP1323429, 2, 2003
- 5c Doi T. Ikeura Y. Natsugari H. Patent WO1999047132, 1, 1999
- 6a Natsugari H. Ikeura Y. Kiyota Y. Ishichi Y. Ishimaru T. Saga O. Shirafuji H. Tanaka T. Kamo I. J. Med. Chem. 1995; 38: 3106
- 6b Natsugari H. Ikeura Y. Kamo I. Ishimaru T. Ishichi Y. Fujishima A. Tanaka T. Kasahara F. Kawada M. Doi T. J. Med. Chem. 1999; 42, 3982
- 6c Humphrey JM. Curr. Top. Med. Chem. 2003; 3: 1423
- 7 Venkova K. Sutkowski-Markmann DM. Greenwood-Van Meerveld B. J. Pharmacol. Exp. Ther. 2002; 300: 1046
- 8 Dress K. Johnson T. Plewe M. Tanis S. Zhu H. Patent US2007099915, 2, 2007
- 9 Singh P. Chorell E. Krishnan KS. Kindahl T. Åden J. Wittung-Stafshede P. Almqvist FK. Org. Lett. 2015; 17: 6194
- 10a Ockenden W. Schofield K. J. Chem. Soc. 1953; 3914
- 10b Schofield K. Theoba RS. J. Chem. Soc. 1951; 2992
- 11a Fisyuk AS. Bundel’ YG. Chem. Heterocycl. Compd. 1999; 35: 125
- 11b Fissyuk AS. Vorontsova MA. Temnikov DV. Tetrahedron Lett. 1996; 37: 5203
- 11c Fisyuk AS. Mendeleev Commun. 1998; 8: 12
- 11d Fisyuk AS. Bogza YP. Poendaev NV. Goncharov DS. Chem. Heterocycl. Compd. 2010; 46: 844
- 11e Goncharov DS. Kostuchenko AS. Fisyuk AS. Chem. Heterocycl. Compd. 2009; 45: 793
- 11f Goncharov DS. Garkushenko AK. Savelieva AP. Fisyuk AS. ARKIVOC 2015; 176
- 12a Fisyuk AS. Kulakov IV. Goncharov DS. Nikitina OS. Bogza YP. Shatsauskas AL. Chem. Heterocycl. Compd. 2014; 50: 217
- 12b Kulakov IV. Matsukevich MV. Shulgau ZT. Sergazy S. Seilkhanov TM. Puzari A. Fisyuk AS. Chem. Heterocycl. Compd. 2015; 51: 991
- 13 Kulakov IV. Nikitina OS. Fisyuk AS. Goncharov DS. Shul’gau ZT. Gulyaev AE. Chem. Heterocycl. Compd. 2014; 50: 670
- 14 Clark RL. Pessolano AA. Witzel B. Lanza T. Shen TY. J. Med. Chem. 1978; 21: 1158
- 15a Bogza SL. Kobrakov KI. Malienko AA. Perepichka IF. Sujkov SY. Bryce MR. Lyubchik SB. Batsanov AS. Bogdan NM. Org. Biomol. Chem. 2005; 3: 932
- 15b Zinchenko SY. Efimenko RA. Suikov SY. Kobrakov KI. Bogza SL. Chem. Heterocycl. Compd. 2009; 45: 365 (с) Agarwal P. K., Sharma S. K., Sawant D., Kundu B.; Tetrahedron; 2009, 65: 1153
- 15c Youn SW. Bihn JH. Tetrahedron Lett. 2009; 50: 4598
- 15d Zhang X. Xu X. Yu L. Zhao Q. Tetrahedron Lett. 2014; 55: 2280
- 16 CCDC 1518432 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures