Monitoring of Catalyst-Free Microwave-Assisted MCR-Type Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives Using Raman Spectrometry

Abstract

In order to prepare an array of β-cyanoenamine derivatives as potential precursors of heterocyclic systems with pharmaceutical interest, the synthesis of fifteen polyfunctionalized 4H-chromenes was realized via a microwave-assisted and catalyst-free three-component reaction. Microwave-heated reactions were monitored by Raman spectroscopy, enabling a fast and efficient setting of the process parameters. This study confirms that this monitoring tool may have some limitations linked to homogeneity of reaction medium. This work also investigates the use of some bio-sourced and sustainable solvents currently studied in many works. Ethanol remains the most suitable for this synthesis.

Key words

microwave - Raman spectroscopy - real-time monitoring - multicomponent reaction - catalyst free - 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

Publikationsverlauf

Eingereicht: 20. Juni 2022

Angenommen nach Revision: 04. Juli 2022

Accepted Manuscript online:
04. Juli 2022

Artikel online veröffentlicht:
22. August 2022

• References

• 1 Foucourt A, Dubouilh-Benard C, Chosson E, Corbière C, Buquet C, Iannelli M, Leblond B, Marsais F, Besson T. Tetrahedron 2010; 66: 4495
• 2 Loidreau Y, Marchand P, Dubouilh-Benard C, Nourrisson M.-R, Duflos M, Lozach O, Loaëc N, Meijer L, Besson T. Eur. J. Med. Chem. 2012; 58: 171
• 3 Foucourt A, Hédou D, Dubouilh-Benard C, Girard A, Taverne T, Casagrande A.-S, Désiré L, Leblond B, Besson T. Molecules 2014; 19: 15411
• 4 Loidreau Y, Nourrisson M.-R, Fruit C, Corbière C, Marchand P, Besson T. Pharmaceuticals 2020; 13: 202
• 5 Pratap R, Ram VJ. Chem. Rev. 2014; 114: 10476
• 6 Virdi HS, Sharma S, Mehndiratta S, Bedi PM. S, Nepali K. J. Enzyme Inhib. Med. Chem. 2015; 30: 730
• 7 Kaur R, Naaz F, Sharma S, Mehndiratta S, Gupta MK, Bedi PM. S, Nepali K. Med. Chem. Res. 2015; 24: 3334
• 8 Kaur M, Kaur A, Mankotia S, Singh H, Singh A, Singh JV, Gupta MK, Sharma S, Nepali K, Bedi PM. S. Eur. J. Med. Chem. 2017; 131: 14
• 9 Maharramov A, Kaya R, Taslimi P, Kurbanova M, Sadigova A, Farzaliyev V, Sujayev A, Gulçin I. Arch. Pharm. Chem. Life Sci. 2019; 352: e1800317
• 10 Paczkowski IM, Guedes EP, Mass EB, de Menezes EW, Marques LM, Mantovani MS, Russowsky D. J. Heterocycl. Chem. 2020; 57: 2597
• 11 Raj V, Lee J. Front. Chem. 2020; 8: 623
• 12 Ye Z, Xu R, Shao X, Xu X, Li Z. Tetrahedron Lett. 2010; 51: 4991
• 13 Xu J.-C, Li W.-M, Zheng H, Lai Y.-F, Zhang P.-F. Tetrahedron 2011; 67: 9582
• 14 Kazemi B, Javanshir S, Maleki A, Safari M, Khavasi HR. Tetrahedron Lett. 2012; 53: 6977
• 15 Revanna CN, Swaroop TR, Raghavendra GM, Bhadregowda DG, Mantelingu K, Rangappa KS. J. Heterocycl. Chem. 2012; 49: 851
• 16 Azath IA, Puthiaraj P, Pitchumani K. ACS Sustainable Chem. Eng. 2013; 1: 174
• 17 Wagh YB, Tayade YA, Padvi SA, Patil BS, Patil NB, Dalal DS. Chin. Chem. Lett. 2015; 26: 12731277
• 18 Beheshtiha SY, Oskooie HA, Pourebrahimi FS, Zadsirjan V. Chem. Sci. Trans. 2015; 4: 689
• 19 Shirini F, Daneshvarb N. RSC Adv. 2016; 6: 110190
• 20 Yousefi MR, Goli-Jolodar O, Shirini F. Bioorg. Chem. 2018; 81: 326
• 21 Saini S, Kaur MN, Singh N. Green Chem. 2020; 22: 956
• 22 Khazaee A, Jahanshahi R, Sobhani S, Skibsted J, Sansano JM. Green Chem. 2020; 22: 4604
• 23 Zanin LL, Jimenez DE. Q, de Jesus MP, Diniz LF, Javier E, Porto AL. M. J. Mol. Struct. 2021; 1223: 129226
• 24 Khaksar S, Rouhollahpour A, Talesh SM. J. Fluorine Chem. 2012; 141: 11
• 25 Lü C.-W, Wang J.-J, Li F, Yu S.-J, An Y. Res. Chem. Intermed. 2018; 44: 1035
• 26 Hédou D, Deau E, Dubouilh-Benard C, Sanselme M, Martinet A, Chosson E, Levacher V, Besson T. Eur. J. Org. Chem. 2013; 7533
• 27 Deau E, Hédou D, Chosson E, Levacher V, Besson T. Tetrahedron Lett. 2013; 54: 3518
• 28 Elie J, Fruit C, Besson T. Molecules 2021; 26: 3540
• 29 Campos JF, Loubidi M, Scherrmann M.-C, Berteina-Raboin S. Molecules 2018; 23: 684
• 30 Campos JF, Berteina-Raboin S. Catalysts 2020; 10: 429
• 31 Campos JF, Cailler M, Claudel R, Prot B, Besson T, Berteina-Raboin S. Molecules 2021; 26: 1074
• 32 Stellman CM, Aust JF, Myrick ML. Appl. Spectrosc. 1995; 49: 392
• 33 Pivonka DE. Empfield J. R. Appl. Spectrosc. 2004; 58: 41
• 34 Barnard TM, Leadbeater NE. Chem. Commun. 2006; 3615
• 35 Leadbeater NE, Smith RJ. Org. Lett. 2006; 8: 4589
• 36 Leadbeater NE, Smith RJ, Barnard TM. Org. Biomol. Chem. 2007; 5: 822
• 37 Leadbeater NE, Schmink JR. Nat. Protoc. 2008; 3: 1
• 38 Schmink JR, Holcomb JL, Leadbeater NE. Chem. Eur. J. 2008; 17: 9943
• 39 Schmink JR, Holcomb JL, Leadbeater NE. Org. Lett. 2009; 11: 365
• 40 Schmink JR, Leadbeater NE. Org. Biomol. Chem. 2009; 7: 3842
• 41 Leadbeater NE. Chem. Commun. 2010; 46: 6693
• 42 Hamlin TA, Leadbeater NE. Beilstein J. Org. Chem. 2013; 9: 1843
• 43 Calvino-Casilda V, Bañares MA. Catal. Today 2012; 187: 191
• 44 Christiaens S, Vantyghem X, Radoiu M, Vanden Eynde JJ. Molecules 2014; 19: 9986
• 45 Trenfield SJ, Januskaite P, Goyanes A, Wilsdon D, Rowland M, Gaisford S, Basit AW. Pharmaceutics 2022; 14: 589
• 46 Thobakgale SL, Ombinda-Lemboumba S, Mthunzi-Kufa P. Molecules 2022; 27: 2554
• 47 Clarke CJ, Tu W.-C, Levers O, Bröhl A, Hallett JP. Chem. Rev. 2018; 118: 747
• 48 Winterton N. Clean Techn. Environ. Policy 2021; 23: 2499
• 49 Campos JF, Berteina-Raboin S. Catalysts 2019; 9: 840
• 50 Campos JF, Ferreira V, Berteina-Raboin S. Catalysts 2021; 11: 222
• 51 Campos JF, Berteina-Raboin S. Catalysts 2022; 12: 48