SYNTHETIC APPROACHES TO HYDROGENIZED PYRIDYL[b]AZEPINE AND THEIR BENZENELYLATED ANALOGUES
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Keywords

pyrido[b]azepines, catalytic cyclization, radical reactions, Beckmann rearrangement, cycloalkylations.

How to Cite

Danyliuk, I., & Vovk, M. (2020). SYNTHETIC APPROACHES TO HYDROGENIZED PYRIDYL[b]AZEPINE AND THEIR BENZENELYLATED ANALOGUES. Ukrainian Chemistry Journal, 86(8), 101-110. https://doi.org/10.33609/2708-129X.86.8.2020.101-110

Abstract

Pyrido[b]azepines are represented in the literature by four types of isomeric structures: pyrido[3,2-b] azepines, pyrido[2,3-b]azepines, pyrido[3,4-b] azepines and pyrido[4,3-b ]azepines. They belong to the structural analogues of 1-benzazepine - an attractive class of heterocycles with a strong pharmacological profile. They are also used as important molecular platforms in the construction of bioactive compounds. Analysis of the literature has shown that compounds that contain the pyrido[b]azepine fragment demonstrate antiviral, antimicrobial, and antitumor activity. They are knownas effective inhibitors of R1P1 kinase, ubiquitin- specific proteases (USPS), cyclin-dependent kinase (CDKS), and glycogen synthase kinase 3 (GSK-3), TRPM8 protein, and angiotensin I type 2 (AT2) receptors. Over the last decade, promising pharmacological properties of pyrido[b]azepine derivatives stimulated the development of fundamentally new methods of their synthesis as well as the improvement of known synthetic approaches. In general, among the various methods for the synthesis of hydrogenated pyrido[b] azepines and their benzanelated analogues, priority is currently given to approaches that include the formation of an azepine cycle via the intermolecular formation of C-N and C-C bonds. These mainly include catalytic cyclizations using cobalt, palladium, and rhodium compounds. Reactions of intramolecular radical difluoromethylarylation and diauryl peroxide-initiated radical azepine analelenization of the pyridine fragment are also of great importance. An interesting method for the synthesis of pyrido [2,3-b] azepin-5-one derivatives was developed on the basis of the Friedel-Crafts intramolecular cycloalkylations reaction.

https://doi.org/10.33609/2708-129X.86.8.2020.101-110
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References

1. Driowya M., Saber A., Marzag H., Demange L., Bougrin K., Benhida R. Microwaveassisted syntheses of bioactive sevenmembered, macro-sized heterocycles and their fused derivatives. Molecules. 2016. 21: 1032.
2. Danyliuk I. Yu., Vas’kevich R. I., Vas’kevich A. I., Vovk M. V. Hydrogenated benzazepines: recent advances in the synthesis and study of biological activity. Chemistry of Heterocyclic Compounds. 2019. 55: 802.
3. Patent US 2012/0251497. Zhong, M.; Li, L. Inhibitors of hepatitis C virus. 2012.
4. Patent WO 2019/006291. Kim I.J., Panarese J., Blaisdell T.P., Yu J., Shook B.C., Or, Y.S. Heterocyclic compounds as inhibitors. 2019.
5. Patent WO 2014/072930. Mohamed T., Hosahalli S., Panigrahi S.K. Fused pyridine derivatives as anti-bacterial agents. 2014.
6. Patent WO 2016/168014. Targeted treatment of leiomyosarcoma / Benhadji K. A., Massard C., Soria J.-C. 2016.
7. Patent WO 2013/016081. Notch pathway signaling inhibitor compound / Hipskind P.A., Stephen-Son G.A. 2013.
8. Patent US 2010/0249109. Substituted tetrahydropyrazolo- pyrido-azepine compounds / Lapierre J.-M., Yang R.-Y., Namdev N., Link J.S. 2010.
9. Patent WO 2017/024315. Heterocyclic thiosemicarbazone derivatives and their therapeutical applications / Tao C., Wang Q., Soon-Shiong P. 2017.
10. Patent WO 2018/073193. Bicyclic pyridine lactams and methods of use thereof / Patel S. 2018.
11. Patent WO 2018/109097. Inhibitors of R1P1 kinase and methods of use thereof / Patel S., Hamilton G. 2018.
12. Patent WO 2017/136727. Compounds, compositions and methods cross reference to related applications / Estrada A. A., Feng J. A., Fox B., Leslie C.P., Lyssikatos J. P., Pozzan A., Sweeney Z.K., De Vi Cente Fidalgo J. 2017.
13. Patent WO 2017/069279. Heterocyclic compound / Katon T., Nakada Y., Saitoh M., Seki T., Yoge T., Yoshikawa M. 2017.
14. Patent WO 2020/033707. Carboxamides as ubiquitin-specific protease inhibitors / Guerin D., Ng P.Y., Wang Z., Shelekhin T., Caravella J., Zablocki M.-M., Downing J. R., Li H., Ioan-Nidis S. 2020.
15. Egert-Schmidt A.-M., Dreher J., Dunkel U., Kohfeld S., Preu L., Weber H., Ehlert J. E., Mutschler B., Totzke F., Schächtele C., Kubbutat M. H. G., Baumann K., Kunick C. J. Identificatio of 2-anilino-9-methoxy-5,7-dihydro-6Hpyrimido[ 5,4-d][1]benzazepin-6-ones as dual PLK1/VEGF-R2-R2 kinase inhibitor chemotypes by structure-based lead generation. Journal of Medicinal Chemistry. 2010. 53: 2433.
16. Patent WO 2014/025651. Chroman derivatives as TRPM8 inhibitors / Biswas K. Brown J., Chen J.J., Gore V.K., Harried S., Horne D.B., Kaller M.R., Ma V. V., Nguyen T. T., Sham K., Zhong W. 2014.
17. Patent WO 2016/113668. Pyrrolidine derivatives as angiotensin II type 2 antagonists / Brown J., Mccazthy T. O., Naylor A., Watts J.P. 2016.
18. Keen S. P., Cowden C. J., Bishop B. C., Brands K. M. J., Davies A. J., Dolling U. H., Lieberman D.R., Stewart G.W. Practical asymmetric synthesis of a non-peptidic αvβ3 antagonist. The Journal of Organic Chemistry. 2005. 70: 1771.
19. Villani F.J. 5-(3-Dimethylaminopropyl)- 2,8-diaza-10,11-dihydro-5H-dibenzo[b,f] azepine. Journal of Medicinal Chemistry. 1967. 10: 497.
20. Garcia P., Evanno Y., George P., Sevrin M., Ricci G., Malacria M., Aubert C., Gandon V. Regioselective Cobalt-Catalyzed formation of bicyclic 3- and 4-aminopyridines. Organic Letters. 2011. 13: 2030.
21. Garcia P., Evanno Y., George P., Sevrin M., Ricci G., Malacria M., Aubert C., Gandon, V. Synthesis of aminopyridines and aminopyridones by Cobalt-catalyzed [2+2+2] cycloadditions involving yneynamides: scope, limitations, and mechanistic insights. Chemistry a European Journal. 2012. 18: 4337.
22. Hu T., Ye Z., Zhu K., Xu K., Wu Y., Zhang F. Synthesis of tribenzo[b,d,f]azepines via cascade π-extended decarboxylative annulation involving cyclic diaryliodonium salts. Organic Letters. 2020. 22: 505.
23. Frick J. J., Ly C. Q., Schwarz J. B. Synthesis of tricyclic 1,2,3-triazolopyridines. Synthesis.
2015. 47: 2593.
24. Bendorf H. D., Ruhl K. E., Shurer A. J., Shaffer J. B., Duffin T. O., LaBarte T. L., Maddock M. L., Wheeler O. W. Aminedirected intramolecular hydroacylation of alkenes and alkynes. Tetrahedron Letters. 2012. 53: 1275.
25. Lam H., Tsoung J., Lautens M. J. Synthesis of pyridobenzazepines using a one-pot Rh/Pd-catalyzed process. The Journal of Organic Chemistry. 2017. 82: 6089.
26. Tsoung J., Panteleev J., Tesch M., Lautens M. J. Multicomponent-multicatalyst reactions (MC)2R: Efficient dibenzazepine synthesis. Organic Letters. 2014. 16: 110.
27. Saget T., Cramer N. Enantioselective C-H arylation strategy for functionalized dibenzazepinones with quaternary stereocenters. Angewandte International Edition Chemie. 2013. 52: 7865.
28. Xiong P., Xu H.-H., Song J., Xu H.-C. Electrochemical difluoromethylarylation of alkynes. Journal of the American Chemical Society. 2018. 140: 2460.
29. Petit L., Botez I., Tizot A., Zard S. Z. A flexible radical approach to 5-substituted 4,5-dihydro-3H-pyrido[4,3-b]azepin- 2-ones. Some mechanistic observations on the radical cyclisation-aromatisation process. Tetrahedron Letters. 2012. 53: 3220.
30. Muylaert K., Jatczak M., Wuyts B., De Coen L.M., Van Hecke K., Loones H., Keemink J., Garcia D., Mangelinckx S., Annaert P., Stevens C.V. Synthesis and early ADME evaluation of a novel scaffold, tetrahydro- 6H-pyrido[3,2-b]azepin-6-one. Synlett. 2014. 25: 1443.
31. Abd El-Aal H.A.K., Khalaf A.A. Friedel- Crafts chemistry. Part 40. An expedient novel synthesis of some dibenz-azepines, -azocines, 11H-benzo[f]pyrido[2,3-b] azepines and 6H-benzo[g]pyrido[2,3-c] azocines. Arkivoc. 2013. 4: 306.

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