A Domino Reaction for the Synthesis of Novel 1,3-Dihydrofuro[3,4-c]pyridines from Pyridoxal and Ketones

Abstract

A convenient domino route for the synthesis of novel 1,3-dihydrofuro[3,4-c]pyridines from pyridoxal and alkyl, aryl or heteroaryl ketones under basic conditions is reported. A series of nine derivatives is obtained in 53–90% yields after stirring reactants for 48 hours at room temperature. Most products are easily isolated by filtration followed by recrystallization from ethanol. All products were fully characterized by FTIR, HRMS, and ¹H and ¹³C NMR spectroscopy. The X-ray crystal structure of a representative example of the 1,3-dihydrofuro[3,4-c]pyridine series is also presented.

Key words

biobased molecules - Claisen–Schmidt condensation - domino reactions - fused-ring systems - oxa-Michael addition - vitamins

• References

• 1 Liang J, Han Q, Tan Y, Ding H, Li J. Front. Mol. Biosci. 2019; 6: 4
• 2 Du Y.-L, Ryan KS. Nat. Prod. Rep. 2019; 36: 430
• 3 McCormick DB, Chen H. J. Nutr. 1999; 129: 325
• 4a Mandal S, Modak R, Sikdar Y, Naskar B, Goswami S. J. Mol. Struct. 2014; 1074: 271
• 4b Pereira MB, Fontana LA, Siqueira JD, Auras BL, Da Silva MP, Neves A, Gabriel P, Terenzi H, Iglesias BA, Back DF. Inorg. Chim. Acta 2018; 469: 561
• 4c Jakusch T, Kozma K, Enyedy ÈA, May NV, Roller A, Kowol CR, Keppler BK, Kiss T. Inorg. Chim. Acta 2018; 472: 243
• 5a Grigg R, Armstrong P. Tetrahedron 1989; 45: 7581
• 5b Selva E, Castelló LM, Aracil JM, Selva V, Nájera C, Foubelo F, Sansano JM. Tetrahedron 2017; 73: 6840
• 6a Brufola G, Fringuelli F, Piermatti O, Pizzo F. Heterocycles 1997; 45: 1715
• 6b Zhuravel IO, Kovalenko SM, Ivachtchenko AV, Chernykh VP, Shinkarenko PE. J. Heterocycl. Chem. 2004; 41: 517
• 6c Zhuravel IO, Kovalenko SM, Zaremba OV, Detistov OS, Kovalenko SS, Chernykh VP. Synth. Commun. 2008; 38: 3778
• 6d Detistov OS, Panda SS, Steel PJ, Asiri AM, Hall D, Katritzky AR. Synlett 2014; 25: 2654
• 7 Kim Y.-C, Jacobson KA. Synthesis 2000; 119
• 8a Sosnovskikh VY, Korotaev VY, Barkov AY, Sokovnina AA, Kodess MI. J. Fluorine Chem. 2012; 141: 58
• 8b Pereira MB, Kopp CR, Fontana LA, de Oliveira GM, Back DF, Piquini PC, Villetti MA. New J. Chem. 2014; 38: 3092
• 9a Chen J, Gong X, Li J, Li Y, Ma J, Hou C, Zhao G, Yuan W, Zhao B. Science 2018; 360: 1438
• 9b Chen J, Liu YE, Gong X, Shi L, Zhao B. Chin. J. Chem. 2019; 37: 103
• 10a Müller IB, Wu F, Bergmann B, Knöckel J, Walter RD, Gehring H, Wrenger C. PLoS One 2009; 4: e4406
• 10b Brokamp R, Bergmann B, Müller IB, Bienz S. Bioorg. Med. Chem. 2014; 22: 1832
• 11a Zhuravel IO, Kovalenko SM, Ivachtchenko AV, Balakin KV, Kazmirchuk VV. Bioorg. Med. Chem. Lett. 2005; 15: 5483
• 11b Heidari A, Noshiranzadeh N, Haghi F, Bikas R. Microb. Pathogenesis 2017; 112: 103
• 12 Kesel AJ. Bioorg. Med. Chem. 2003; 11: 4599
• 13 Taguchi T, Sugiura M, Hamada Y, Miwa I. Eur. J. Pharmacol. 1999; 378: 283
• 14 Garay RP, Nazaret C, Diez J, Etienne A, Bourgain R, Braquet P. Biochem. Pharmacol. 1984; 33: 2013
• 15a Page J, Page K, Cornett G. Eur. Pat. Appl EP 1951264, 2008
• 15b Bagrov AY, Dmitrieva RI, Dorofeeva NA, Fedorova OV, Lopatin DA, Lakatta EG, Droy-Lefaix MT. J. Hypertens. 2000; 18: 209
• 16 Izuhara Y, Nangaku M, Takizawa S, Takahashi S, Shao J, Oishi H, Kobayashi H, van Ypersele de Strihou C, Miyata T. Nephrol. Dial. Transpl. 2008; 23: 497
• 17 Salunke DB, Yoo E, Shukla NM, Balakrishna R, Malladi SS, Serafin KJ, Day VW, Wang X, David SA. J. Med. Chem. 2012; 55: 8137
• 18a Kibardina LK, Chumakova LV, Gazizov AS, Burilov AR, Pudovik MA. Synthesis 2015; 47: 721
• 18b Zhuravel IO, Kovalenko SM, Zaremba OV, Detistov OS, Kovalenko SS, Chernykh VP. Mendeleev Commun. 2019; 29: 116
• 19a Franco MS. F, Casagrande GA, Raminelli C, Moura S, Rossatto M, Quina FH, Pereira CM. P, Flores AF. C, Pizzuti L. Synth. Commun. 2015; 45: 692
• 19b dos Santos EF. S, Cury NM, do Nascimento TA, Raminelli C, Casagrande GA, Pereira CM. P, Simionatto E, Yunes JA, Pizzuti L. J. Braz. Chem. Soc. 2017; 28: 217
• 19c Favarin LR. V, Rosa PP, Pizzuti L, Machulek AJr, Caires AR. L, Bezerra LS, Pinto LM. C, Maia G, Gatto CC, Back DF, dos Anjos A, Casagrande GA. Polyhedron 2017; 121: 185
• 19d Albuquerque DY, Damim AC, Faoro E, Casagrande GA, Back DF, Moura S, Pereira CM. P, de Oliveira KM. P, Pizzuti L. J. Braz. Chem. Soc. 2020; 31: 746
• 20 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
• 21 Farrugia LJ. J. Appl. Cryst. 1997; 30: 565
• 22 CCDC 1995481 (3c) 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.