Acid-Mediated Synthesis of Chromeno[2,3-b]pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives

Abstract

A convenient and effective protocol has been proposed for the synthesis of chromeno[2,3-b]pyridine derivatives via the CF₃SO₃H-catalyzed annulation of substituted 2-amino-3-formylchromones and various 1-(methylthio)-2-nitroenamine derivatives. This method is time-efficient, convenient, high-yielding, and exhibits a good functional group compatibility.

Key words

2-amino-3-formylchromone derivatives - chromeno[2,3-b]pyridine derivatives - (E)-N-methyl-1-(methylthio)-2-nitroethenamine (NMSM)

Publication History

Received: 21 January 2022

Accepted after revision: 07 March 2022

Accepted Manuscript online:
07 March 2022

Article published online:
25 April 2022

• References and Notes

• 1 Reis J, Gaspar A, Milhazes N, Borges F. J. Med. Chem. 2017; 60: 7941
• 2a Zhang M, Gong Y, Zhou W, Zhou Y, Liu X.-L. Org. Chem. Front. 2021; 8: 3968
• 2b Langer P. Synlett 2022; 33: 207
• 3 Beyett TS, Gan X, Reilly SM, Gomez AV, Chang L, Tesmer JJ. G, Saltiel AR, Showalter HD. Bioorg. Med. Chem. 2018; 26: 5443
• 4 Nohara A, Ishiguro T, Ukawa K, Sugihara H, Maki Y, Sanno Y. J. Med. Chem. 1985; 28: 559
• 5a Azuine MA, Tokuda H, Takayasu J, Enjyo F, Mukainaka T, Konoshima T, Nishino H, Kapadia GJ. Pharmacol. Res. 2004; 49: 161
• 5b Bizarro A, Sousa D, Lima RT, Musso L, Cincinelli R, Zuco V, De Cesare M, Dallavalle S, Vasconcelos MH. Molecules 2018; 23: 407
• 5c Landriscina M, Prudovsky I, Carreira CM, Soldi R, Tarantini F, Maciag T. J. Biol. Chem. 2000; 275: 32753
• 6 Brötz-Oesterhelt H, Knezevic I, Bartel S, Lampe T, Warnecke-Eberz U, Ziegelbauer K, Häbich D, Labischinski H. J. Biol. Chem. 2003; 278: 39435
• 7 Dimitriadou E, Raftopoulou M, Kasapidou PM, Tsoleridis CA, Stephanidou-Stephanatou J, Hadjipavlou-Litina DJ, Kontogiorgis C, Pritsa A, Papadopoulos A. ARKIVOC 2014; 372
• 8 Anderson DR, Hegde S, Reinhard E, Gomez L, Vernier WF, Lee L, Liu S, Sambandam A, Snider PA, Masih L. Bioorg. Med. Chem. Lett. 2005; 15: 1587
• 9a Oset-Gasque MJ, González MP, Pérez-Peña J, García-Font N, Romero A, del Pino J, Ramos E, Hadjipavlou-Litina D, Soriano E, Chioua M, Samadi A, Raghuvanshi DS, Singh KN, Marco-Contelles J. Eur. J. Med. Chem. 2014; 74: 491
• 9b Maalej E, Chabchoub F, Oset-Gasque MJ, Esquivias-Pérez M, González MP, Monjas L, Pérez C, de los Ríos C, Rodríguez-Franco MI, Iriepa I, Moraleda I, Chioua M, Romero A, Marco-Contelles J, Samadi A. Eur. J. Med. Chem. 2012; 54: 750
• 10 Waldmann H, Karunakar GV, Kumar K. Org. Lett. 2008; 10: 2159
• 11 Abdel-Rahman A.-RH, Girges MM, El-Ahl A.-AS, Sallam LM. Heteroat. Chem. 2006; 17: 2
• 12 Ibrahim MA. M. Eur. J. Chem. 2010; 1: 124-128
• 13 Saigal Saigal, Khan S, Rahman H, Shafiullah Shafiullah, Khan MM. RSC Adv. 2019; 9: 14477
• 14 Ryan CW. GB 2134521A 1984
• 15 Crookes DL. GB 2217713A 1989
• 16a Feng Y, Zou M, Song R, Shao X, Li Z, Qian X. J. Org. Chem. 2016; 81: 10321
• 16b Yang H, Xiong D, Peng Y, Shao X, Xu X, Li Z. J. Heterocycl. Chem. 2021; 58 ; in press DOI: DOI: 10.1002/jhet.4408.
• 16c Chen X.-f, Ren C, Xu X.-y, Shao X.-s, Li Z. Tetrahedron Lett. 2017; 58: 1433
• 16d Wang F, Wu W, Xu X, Shao X, Li Z. Tetrahedron Lett. 2018; 59: 2506
• 16e Zhu F, Zou M, Shao X, Li Z. RSC Adv. 2015; 5: 61752
• 17 CCDC 2141783 and 2141782 contain 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/structures.
• 18 A mixture of substituted 4-oxo-4H-1-benzopyran-3-carbonitriles (10 mmol) and concentrated NH₄OH solution (10 mL) was stirred at room temperature until the solid dissolved and then was diluted with water (10 mL). The product obtained was filtered and recrystallized from ethanol to give 1 as yellow crystals
• 19 For Aliphatic AminesTo the solution of compound 1,1-bis(methylthio)-2-nitroethylene (BMTNE, 15 mmol) in acetonitrile (40 mL), aliphatic amine (15 mmol) was added dropwise at 0 °C. The resulting solution was stirred at room temperature for 24 h. The reaction was evaporated to dryness, and the residue was purified by chromatography over silica gel to give the corresponding product.For Benzylamines and Heterocyclic AminesCorresponding amine (15 mmol) was added to the solution of compound BMTNE (15 mmol) in ethanol (40 mL). The resulting solution was stirred under reflux for 12 h. The reaction was evaporated to dryness, and the residue was purified by chromatography over silica gel to give the corresponding product.