Abstract
Green chemistry aims at developing reactions that are cheap, clean and use less energy. For that, multicomponent reactions are drawing attention, yet, actual methods involve complicated work-ups, hazardous solvents, toxic catalysts, high catalyst loads, harsh reaction conditions and tedious catalyst preparation. Here, we demonstrate that the commercially available reagent, 9-mesityl-10 methylacridinium perchlorate (Acr+-Mes ClO4−), can serve as a photocatalyst in the presence of a blue lamp light source, promoting the synthesis of 2-amino-4H-chromenes via a multicomponent reaction with low catalyst loadings. A wide range of aromatic aldehydes readily undergo condensation with malononitrile and ArOH-type structural motifs under mild conditions to afford the products in 76–95% yield within 60 min.
Similar content being viewed by others
References
Amr A-GE, Mohamed AM, Mohamed SF, Abdel-Hafez NA, Hammam AE-FG (2006) Anticancer activities of some newly synthesized pyridine, pyrane, and pyrimidine derivatives. Bioorg Med Chem 14:5481–5488. https://doi.org/10.1016/j.bmc.2006.04.045
Baghbanian SM, Rezaei N, Tashakkorian H (2013) Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media. Green Chem 15:3446–3458. https://doi.org/10.1039/C3GC41302K
Billing MBK, Agnihotri PK, Kaur N, Singh N, Jang DO (2018) Ionic liquid-coated carbon nanotubes as efficient metal free catalysts for the synthesis of chromene derivatives. ACS Sustain Chem Eng 6:3714–3722. https://doi.org/10.1021/acssuschemeng.7b04048
Bonsignore L, Loy G, Secci D, Calignano A (1993) Synthesis and pharmacological activity of 2-oxo-(2H)1-benzopyran-3-carboxamide derivatives. Eur J Med Chem 28:517–520. https://doi.org/10.1016/0223-5234(93)90020-f
Brahmachari G, Banerjee B (2014) Facile and one-pot access to diverse and densely functionalized 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic scaffolds via an eco-friendly multicomponent reaction at room temperature using urea as a novel organo-catalyst. ACS Sustain Chem Eng 2:411–422. https://doi.org/10.1021/sc400312n
Desimoni G, Faita G, Quadrelli P (2018) Forty years after “heterodiene syntheses with α, β-unsaturated carbonyl compounds”: enantioselective syntheses of 3,4-dihydropyran derivatives. Chem Rev 118:2080–2248. https://doi.org/10.1021/acs.chemrev.7b00322
Dömling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112:3083–3135. https://doi.org/10.1021/cr100233r
Grandjean J-MM, Nicewicz DA (2013) Synthesis of highly substituted tetrahydrofurans by catalytic polar-radical-crossover cycloadditions of alkenes and alkenols. Angew Chem Int Ed 52:3967–3971. https://doi.org/10.1002/ange.201210111
Hameed AMA (2018) Efficient synthesis of pyrano[2,3-b]pyridine derivatives using microwave or solar energy. Environ Chem Lett 16:1423–1427. https://doi.org/10.1007/s10311-018-0744-5
He R, Chen X, Li Y, Liu Q, Liao C, Chen L, Huang Y (2019) NH4I-promoted and H2O-controlled intermolecular bis-sulfenylation and hydroxysulfenylation of alkenes via a radical process. J Org Chem 4:8750–8758. https://doi.org/10.1021/acs.joc.9b01047
Horváth IT, Anastas PT (2007) Innovations and green chemistry. Chem Rev 107:2169–2173. https://doi.org/10.1021/cr078380v
Hostetler G, Dunn D, McKenna BA, Kopec K, Chatterjee S (2014) 1-Thia-4,7-diaza-spiro[4.4]nonane-3,6-dione: a structural motif for 5-hydroxytryptamine 6 receptor antagonism. Chem Biol Drug Des 83:149–153. https://doi.org/10.1111/cbdd.12240
Jafari AA, Ghadami M (2016) High yield room temperature synthesis of pyranochromenes in neutral cetyltrimethylammonium bromide micellar media. Environ Chem Lett 14:215–221. https://doi.org/10.1007/s10311-015-0546-y
Kantharaju K, Khatavi S (2018) Microwave accelerated synthesis of 2-amino-4H-chromenes catalyzed by WELFSA: a green protocol. ChemistrySelect 3:5016–5024. https://doi.org/10.1002/slct.201800096
Kaur R, Naaz F, Bedi PMS, Sharma S, Nepali K, Mehndiratta S, Gupta MK (2015) Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies. Med Chem Res 24:3334–3349. https://doi.org/10.1007/s00044-015-1382-0
Khaligh NG, Mihankhah T, Johan MR (2019) Synthesis of new low-viscous sulfonic acid-functionalized ionic liquid and its application as a Brönsted liquid acid catalyst for the one-pot mechanosynthesis of 4H-pyrans through the ball milling process. J Mol Liq 277:794–804. https://doi.org/10.1016/j.molliq.2019.01.024
Khan AT, Lal M, Ali S, Khan MM (2011) One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst. Tetrahedron Lett 52:5327–5332. https://doi.org/10.1016/j.tetlet.2011.08.019
Khoobi M, Alipour M, Sakhteman AH, Moradi A, Ghandi M, Emami S, Nadri H, Foroumadi A, Shafiee A (2013) Design, synthesis, biological evaluation and docking study of 5-oxo-4,5-dihydropyrano[3,2-c]chromene derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors. Eur J Med Chem 68:260–269. https://doi.org/10.1016/j.ejmech.2013.07.038
Khurana JM, Kumar S (2009) Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4 dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetrahedron Lett 50:4125–4127. https://doi.org/10.1016/j.tetlet.2009.04.125
Khurana JM, Nand B, Saluja P (2010) DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4Hbenzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium. Tetrahedron 66:5637–5641. https://doi.org/10.1016/j.tet.2010.05.082
Maryam Mashhadinezhad M, Manouchehr Mamaghani M, Mehdi Rassa M, Farhad Shirini F (2019) A facile green synthesis of chromene derivatives as antioxidant and antibacterial agents through a modified natural soil. ChemistrySelect 4:4920–4932. https://doi.org/10.1002/slct.201900405
Moosavi-Zare AR, Zolfigol MA, Khaledian O, Khakyzadeh V, Farahani MD, Beyzavi MH, Kruger HG (2014) Tandem Knoevenagel–Michael–cyclocondensation reaction of malononitrile, various aldehydes and 2-naphthol over acetic acid functionalized ionic liquid. Chem Eng J 248:122–127. https://doi.org/10.1016/j.cej.2014.03.035
Morgan LR, Jursic BS, Hooper CL, Neumann DM, Thangaraj K, Leblance B (2002) Anticancer activity for 4,4’-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) analogues and their abilities to interact with lymphoendothelial cell surface markers. Bioorg Med Chem Lett 12:3407–3411. https://doi.org/10.1016/S0960-894X(02)00725-4
Mosaddegh E (2013) Ultrasonic-assisted preparation of nano eggshell powder: a novel catalyst in green and high efficient synthesis of 2-aminochromenes. Ultrason Sonochem 20:1436–1441. https://doi.org/10.1016/j.ultsonch.2013.04.008
Nadaf AN, Shivashankar K (2018) Visible light-induced synthesis of biscoumarin analogs under catalyst-free conditions. J Heterocyclic Chem 55:1375–1381. https://doi.org/10.1002/jhet.3171
Prier CK, Rankic DA, MacMillan DW (2013) Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev 113:5322–5363. https://doi.org/10.1021/cr300503r
Rueping M, Sugiono E, Merino E (2008) Asymmetric organocatalysis: an efficient enantioselective access to benzopyranes and chromenes. Chem Eur J 14:6329–6332. https://doi.org/10.1002/chem.200800836
Sheldon RA, Woodley JM (2018) Role of biocatalysis in sustainable chemistry. Chem Rev 118:801–838. https://doi.org/10.1021/acs.chemrev.7b00203
Shinde S, Damate S, Morbale S, Patil M, Patil SS (2017) Aegle marmelos in heterocyclization: greener, highly efficient, one-pot three-component protocol for the synthesis of highly functionalized 4H-benzochromenes and 4H-chromenes. RSC Adv 7:7315–7328. https://doi.org/10.1039/c6ra28779d
Smith CW, Bailey JM, Billingham MEJ, Chandrasekhar S, Dell CP, Harvey AK, Hicks CA, Kingston AE, Wishart GN (1995) The anti-rheumatic potential of a series of 2,4-di-substituted-4H-naphtho[1,2-b]pyran-3-carbonitriles. Bioorg Med Chem 5:2783–2788. https://doi.org/10.1002/chin.199614148
Wu P, Givskov M, Nielsen TE (2019) Reactivity and synthetic applications of multicomponent petasis reactions. Chem Rev 119:11245–11290. https://doi.org/10.1021/acs.chemrev.9b00214
Yousefi MR, Goli-Jolodar O, Shirini F (2018) Piperazine: an excellent catalyst for the synthesis of 2-amino-3-cyano-4H-pyrans derivatives in aqueous medium. Bioorg Chem 81:326–333. https://doi.org/10.1016/j.bioorg.2018.08.026
Yu L, Lin C, Liao C, Zeng X, Chen X, Zhu Z, Huang Y, Li Y, Chen L (2020) Green chemistry: efficient acetalization of aldehydes with alcohols using the acid red 52 photocatalyst. Environ Chem Lett. https://doi.org/10.1007/s10311-020-00994-y
Zhang G, Zhang Y, Yan J, Chen R, Wang S, Ma Y, Wang R (2012) One-pot enantioselective synthesis of functionalized pyranocoumarins and 2-amino-4H-chromenes: discovery of a type of potent antibacterial agent. J Org Chem 77:878–888. https://doi.org/10.1021/jo202020m
Acknowledgements
The authors are grateful to the funds of Innovation Project of Guang Dong Graduate Education (2020SFKC065), Science Foundation for Young Teachers of Wuyi University (2019td06), the Foundation of the Department of Education of Guangdong Province (2016KCXTD005, 2017KZDXM085, 2018KZDXM070 and 2019KZDXM052) and Innovation Project of Wuyi University Graduate Education (2020XJ012).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Chen, L., Lin, C., Lan, Y. et al. Visible light-induced green synthesis of 2-amino-4H-chromenes. Environ Chem Lett 18, 2157–2163 (2020). https://doi.org/10.1007/s10311-020-01053-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10311-020-01053-2