New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Abstract

Reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole with azlactones under solvent-free conditions with heating furnished tetrahydro-1H-pyrazolo[3,4-b]pyridines. The latter were converted to oxazolo[5,4-b]pyrazolo[4,3-e]pyridines by the action with POCl₃ on air. Further reaction of oxazolo[5,4-b]pyrazolo[4,3-e]pyridines with hydrazine hydrate and alkali led to the formation of 5-amino-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-ones, which reacted with aluminum chloride to yield 3,4-dihydro-5H-pyrazolo[4,3-f][1,7]naphthyridin-5-ones. Some of the synthesized compounds show antioxidant activity or are effective phosphors.

Key words

azlactone - 5-aminopyrazole - antioxidant - fluorescence - rearrangement - naphthyridine - pyrazolo[3,4-b]pyridine - pyridone–pyridol tautomerism

Publication History

Received: 22 October 2023

Accepted after revision: 28 November 2023

Accepted Manuscript online:
28 November 2023

Article published online:
08 January 2024

• References

• 1a Amer MM. K, Aziz MA, Shehab WS, Abdellattif MH, Mouneir SM. J. Saudi Chem. Soc. 2021; 25: 101259
• 1b Torres M, Gil S, Parra M. Curr. Org. Chem. 2005; 9: 1757
• 1c Sośnicki JG, Idzik TJ. Synthesis 2019; 51: 3369
• 1d Biswas A, Maity S, Pan S, Samanta R. Chem. Asian J. 2020; 15: 2092
• 2a Shaabani A, Nazeri MT, Afshari R. Mol. Divers. 2019; 23: 751
• 2b Donaire-Arias A, Montagut AM, de la Bellacasa RP, Estrada-Tejedor R, Teixidó J, Borrell JI. Molecules 2022; 27: 2237
• 2c Smolobochkin AV, Gazizov AS, Garifzyanov AR, Burilov AR, Pudovik MA. Russ. Chem. Bull. 2022; 71: 878
• 3a Shatsauskas AL, Shatalin YV, Shubina VS, Chernenko SA, Kostyuchenko AS, Fisyuk AS. Dyes Pigm. 2022; 204: 110388
• 3b Litvinov VP, Roman SV, Dyachenko VD. Usp. Khim. 2000; 69: 236
• 3c Litvinov VP, Roman SV, Dyachenko VD. Russ. Chem. Rev. 2001; 70: 299
• 3d Dong LH, Coquelet P, Bastide C, Lebecq J.-M, Lebecq J.-C. Chem. Inform. 1981; 12: 39
• 4a Kim HS, Hammill JT, Scott DC, Chen Y, Min J, Rector J, Singh B, Schulman BA, Guy RK. J. Med. Chem. 2019; 62: 8429
• 4b Kim HS, Hammill JT, Scott DC, Chen Y, Rice AL, Pistel W, Singh B, Schulman BA, Guy RK. J. Med. Chem. 2021; 64: 5850
• 4c Zhao B, Li Y, Xu P, Dai Y, Luo C, Sun Y, Ai J, Geng M, Duan W. ACS Med. Chem. Lett. 2016; 7: 629
• 4d Liu FT, Li NG, Zhang YM, Xie WC, Yang SP, Lu T, Shi ZH. Eur. J. Med. Chem. 2020; 186: 111884
• 4e Shi J, Xu G, Zhu W, Ye H, Yang S, Luo Y, Han J, Yang J, Li R, Wei Y, Chen L. Bioorg. Med. Chem. Lett. 2010; 20: 4273
• 4f Lin R, Connolly PJ, Lu Y, Chiu G, Li S, Yu Y, Huang S, Li X, Emanuel SL, Middleton SA, Gruninger RH, Adams M, Fuentes-Pesquera AR, Greenberger LM. Bioorg. Med. Chem. Lett. 2007; 17: 4297
• 4g Witherington J, Bordas V, Gaiba A, Garton NS, Naylor A, Rawlings AD, Slingsby BP, Smith DG, Takle AK, Ward RW. Bioorg. Med. Chem. Lett. 2003; 13: 3055
• 4h Revesz L, Blum E, Di Padova FE, Buhl T, Feifel R, Gram H, Hiestand P, Manning U, Neumann U, Rucklin G. Bioorg. Med. Chem. Lett. 2006; 16: 262
• 4i Park A, Hwang J, Lee JY, Heo EJ, Na YJ, Kang S, Jeong KS, Kim KY, Shin SJ, Lee H. Bioorg. Med. Chem. Lett. 2021; 47: 128226
• 4j Wenglowsky S, Ren L, Ahrendt KA, Laird ER, Aliagas I, Alicke B, Buckmelter AJ, Choo EF, Dinkel V, Feng B, Gloor SL, Gould SE, Gross S, Gunzner-Toste J, Hansen JD, Hatzivassiliou G, Liu B, Malesky K, Mathieu S, Newhouse B, Raddatz NJ, Ran Y, Rana S, Randolph N, Risom T, Rudolph J, Savage S, Selby LT, Shrag M, Song K, Sturgis HL, Voegtli WC, Wen Z, Willis BS, Woessner RD, Wu WI, Young WB, Grina J. ACS Med. Chem. Lett. 2011; 2: 342
• 4k Hoorens MW. H, Ourailidou ME, Rodat T, van der Wouden PE, Kobauri P, Kriegs M, Peifer C, Feringa BL, Dekker FJ, Szymanski W. Eur. J. Med. Chem. 2019; 179: 133
• 4l Sintim HO, Dayal N, Opoku-Temeng C. Patent WO2018183586, 2018
• 4m Sintim HO, Dayal N, Opoku-Temeng C. Patent US 20200308173, 2020
• 4n Jablonski Ph, Nettekoven M, Patiny-Adam A, Ratni H, Stadler H. Patent US 20110257402, 2011
• 4o Zheng B, Peng Y, Wu W, Ma J, Zhang Y, Guo Y, Sun S, Chen Z, Li Q, Hu G. Arch. Pharm. (Weinheim) 2019; 352: 1
• 4p Plemper RK, Lee E, Vernachio J, Bourque E. Patent WO2017196982, 2017
• 4q Uchikawa O, Mitsui K, Asakawa A, Morimoto Sh, Yamamoto M, Kimura H, Moriya T, Mizuno M. Patent US2003187014, 2003
• 5a Okuda K, Matsushita T, Hirota T, Sasaki K. J. Heterocycl. Chem. 2012; 49: 742
• 5b Ferraris D, Ficco RP, Pahutski T, Lautar S, Huang S, Zhang J, Kalish V. Bioorg. Med. Chem. Lett. 2003; 13: 2513
• 5c Tabart M, Picaut G, Lavergne M, Wentzler S, Malleron JL, Dutka-Malen S, Berthaud N. Bioorg. Med. Chem. Lett. 2003; 13: 1329
• 5d Natsugari H, Ikeura Y, Kiyota Y, Ishichi Y, Ishimaru T, Saga O, Shirafuji H, Tanaka T, Kamo I, Doi T, Otsuka M. J. Med. Chem. 1995; 38: 3106
• 6a Zhu W, Wang J, Wang S, Gu Z, Aceña JL, Izawa K, Liu H, Soloshonok VA. J. Fluorine Chem. 2014; 167: 37
• 6b Prakash R, Shekarrao K, Saikia P, Gogoi S, Boruah RC. RSC Adv. 2015; 5: 21099
• 6c Iaroshenko VO, Gevorgyan A, Mkrtchyan S, Grigoryan T, Movsisyan E, Villinger A, Langer P. ChemCatChem 2015; 7: 316
• 7a Shuvalov VYu, Vlasova EY, Zheleznova TY, Fisyuk AS. Beilstein J. Org. Chem. 2023; 19: 1155
• 7b Shuvalov VYu, Samsonenko AL, Rozhkova YuS, Morozov VV, Shklyaev YuV, Fisyuk AS. ChemistrySelect 2021; 6: 11265
• 7c Shuvalov VYu, Chernenko S. А, Shatsauskas AL, Samsonenko AL, Dmitriev MV, Fisyuk AS. Chem. Heterocycl. Compd. 2021; 57: 764
• 7d Shuvalov VYu, Rozhkova YuS, Plekhanova IV, Kostyuchenko AS, Shklyaev YuV, Fisyuk AS. Chem. Heterocycl. Compd. 2022; 58: 7
• 7e Shuvalov VYu, Fisyuk AS. Synthesis 2023; 55: 1267
• 7f Cunha S, Filho RF. D. S, Saraiva KH, Azevedo-Santos AV, Menezes D. Tetrahedron Lett. 2013; 54: 3366
• 7g Chen X, Zhu D, Wang X, Yan S, Lin J. Tetrahedron 2013; 69: 9224
• 7h Van den Eynde JJ, Labuche N, Van Haverbeke Y. Synth. Commun. 1997; 27: 3683
• 7i Worayuthakarn R, Nealmongkol P, Ruchirawat S, Thasana N. Tetrahedron 2012; 68: 2864
• 7j Liu X.-Q, Liu Y, Shao X, Xu Z.-P, Xu X, Li Z. Chin. Chem. Lett. 2016; 27: 7
• 7k Shi F, Zhang J, Tu S, Jia R, Zhang Y, Jiang B, Jiang H. J. Heterocycl. Chem. 2007; 44: 1013
• 8a Komarova ES, Makarov VA, Alekseeva LM, Avramenko GV, Granik VG. Russ. Chem. Bull. 2006; 55: 735
• 8b Cacciari B, Spalluto G. Synth. Commun. 2006; 36: 1173
• 8c Aly AA, El-Emary TI, Mourad AF. E, Khallaf Alyan Z, Bräse S, Nieger M. J. Chem. Res. 2019; 48: 219
• 8d Hussein AM, El-Emary TI. J. Chem. Res. Synop. 1998; 20
• 8e Wise LD, Butler DE, DeWald HA, Lustgarten D, Coughenour LL, Downs DA, Heffner TG, Pugsley TA. J. Med. Chem. 1986; 29: 1628
• 8f Elgemeie GH, Elghandour AH, Hussein AM. Synth. Commun. 2004; 34: 3293
• 9a Krawczyk S, Otto M, Otto A, Coburger C, Krug M, Seifert M, Tell V, Molnár J, Higeroth A. Bioorg. Med. Chem. 2011; 19: 6309
• 9b Wang S, Pan J, Hu Y, Hu H. Synthesis 2005; 753
• 10a Hamama WS, Ibrahim ME, Zoorob HH. Arch. Pharm. (Weinheim) 2012; 345: 468
• 10b Proshchenkova V. А, Shuvalov VYu, Glyzdinskaya LV, Fisyuk AS, Chernenko SA, Khvostov MV, Tolstikova TG, Vorontsova M. А, Sagitullina GP. Chem. Heterocycl. Compd. 2021; 57: 187
• 11 Shatsauskas AL, Zablotskii Y. А, Chernenko S. А, Zheleznova TY, Shuvalov VYu, Kostyuchenko AS, Fisyuk AS. Chem. Heterocycl. Compd. 2021; 57: 1212
• 12a Shatsauskas AL, Mamonova TE, Stasyuk AJ, Chernenko SA, Slepukhin PA, Kostyuchenko AS, Fisyuk AS. J. Org. Chem. 2020; 85: 10072
• 12b Shatsauskas AL, Keyn ES, Stasyuk AJ, Kirnosov SA, Shuvalov VYu, Kostyuchenko AS, Fisyuk AS. Synthesis 2023; 55: in press
• 13a Katritzky AR, Lagowski JM. Adv. Heterocycl. Chem. 1963; 1: 339
• 13b Katritzky AR, Karelson MA, Harris P. Heterocycles 1991; 32: 329
• 13c Savchenko O. А, Musiyak VV, Goncharov DS, Bogza YuP, Shatsauskas AL, Talzi VP, Evdokimov SN, Ulyankin EB, Fisyuk AS. Chem. Heterocycl. Compd. 2020; 56: 1180
• 14a Shatsauskas A, Shatalin Y, Shubina V, Zablodtskii Y, Chernenko S, Samsonenko A, Kostyuchenko A, Fisyuk A. Dyes Pigm. 2021; 187: 109072
• 14b Fisyuk AS, Kulakov IV, Goncharov DS, Nikitina OS, Bogza YP, Shatsauskas AL. Chem. Heterocycl. Compd. 2014; 50: 217
• 14c Shatsauskas AL, Abramov AA, Chernenko SA, Kostyuchenko AS, Fisyuk AS. Synthesis 2020; 52: 227
• 15 Samsonenko AL, Kostyuchenko AS, Zheleznova TY, Shuvalov VYu, Vlasov IS, Fisyuk AS. Synthesis 2022; 54: 3227
• 16 Ganesan A, Heathcock CH. J. Org. Chem. 1993; 58: 6155
• 17 CCDC 2300767 (5g) and 2300766 (7a) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via href="http://www.ccdc.cam.ac.uk/structures">