RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett
DOI: 10.1055/a-2640-2542
DOI: 10.1055/a-2640-2542
letter
[AcMIm]Cl-Catalyzed One-Pot Multicomponent Synthesis of Pyran Chromene Derivatives
Abstract
A sustainable one-pot multicomponent synthesis of dihydropyrano[3,2-c]chromenes and 2-aminochromenes was developed using [AcMIm]Cl, a task-specific acidic ionic liquid catalyst, under mild, solvent-free conditions. The present protocol affords dihydropyrano[3,2-c]chromenes in excellent yields (93–99%) with a short reaction time (4–5 min), and comparable efficiency was observed for the 2-aminochromenes (90–92%). The bifunctional [AcMIm]Cl bears an acidic carboxyl (–COOH) and a basic imidazolium nitrogen, which act synergistically to activate both the aldehyde carbonyl and the malononitrile C–H bond, thereby accelerating the reaction. The major advantages of this method include a simple workup: no volatile organic solvent, and the solid products were purified by recrystallization from hot ethanol without chromatography. These features render the present method environmentally benign and economically advantageous than conventional approaches.
Keywords
Task-specific ionic liquid - [AcMIm]Cl - Dihydropyrano[3,2-c]chromenes - 2-Aminochromenes - One-pot multicomponent reactions - Green synthesisPublikationsverlauf
Eingereicht: 30. April 2025
Angenommen nach Revision: 19. Juni 2025
Accepted Manuscript online:
20. Juni 2025
Artikel online veröffentlicht:
25. Juli 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Younus HA, Al-Rashida M, Hameed A. et al. Expert Opin Ther Pat 2021; 31 (3) 267-289
- 2 Damera T, Pagadala R, Rana S, Jonnalagadda SB. Catalysts 2023; 13 (7) 1034
- 3 Cioc RC, Ruijter E, Orru RV. Green Chem 2014; 16 (6) 2958-2975
- 4 Domling A, Wang W, Wang K. Chem Rev 2012; 112 (6) 3083-3135
- 5 Toure BB, Hall DG. Chem Rev 2009; 109 (9) 4439-4486
- 6 Zhang M, Liu YH, Shang ZR, Hu HC, Zhang ZH. Catal Commun 2017; 88: 39-44
- 7a Zhang M, Fu QY, Gao G. et al. ACS Sustain Chem Eng 2017; 5 (7) 6175-6182
- 7b Lambat TL, Chopra PKPG, Sami HM. Curr Org Chem 2020; 24: 2527-2554
- 8 Kidwai M, Saxena S, Khan MKR, Thukral SS. Bioorg Med Chem Lett 2005; 15: 4295
- 9 Zhang G, Zhang Y, Yan J. et al. J Org Chem 2012; 77: 878
- 10 Cingolani G, Gualtieri F, Pigini M. J Med Chem 1969; 12 (3) 531-532
- 11 Dehkordi MF, Dehghan G, Mahdavi M, Hosseinpour Feizi MA. Spectrochim Acta A Mol Biomol Spectrosc 2015; 145: 353
- 12 Bedair AH, Emam HA, El-Hady NA, Ahmed KAR, El-Agrody AM. Farmaco 2001; 56: 965
- 13 Khafagy MM, Abd El-Wahab AHF, Eid FA, El-Agrody AM. Farmaco 2002; 57: 715
- 14 Khoobi M, Alipour M, Sakhteman A. et al. Eur J Med Chem 2013; 68: 260
- 15 Smith CW, Bailey JM, Billingham MEJ. et al. Bioorg Med Chem Lett 1995; 5: 2783
- 16 El-Agrody AM, Halawaa AH, Fouda AM, Al-Dies AAMJ. Saudi Chem Soc 2017; 21: 82
- 17 Rafinejad A, Fallah-Tafti A, Tiwari R. et al. DARU J Pharm Sci 2012; 20: 100
- 18 Dong-Oh M, Choi Y, Nam-Duk K, Yeong-Min P, Gi-Young K. Int Immunopharmacol 2007; 7: 506
- 19 Abdelrazeka FM, Metza P, Farrag EK. Arch Pharm Pharm Med Chem 2004; 337: 482
- 20 El-Agrody AM, Abd-Rabboh HSM, Al-Ghamdi AM. Med Chem Res 2013; 22: 1339
- 21 Smith PW, Sollis SL, Howes PD. J Med Chem 1998; 41: 787
- 22 Wang HJ, Lu J, Zhang ZH. Monatsh Chem 2010; 141: 1107-1112
- 23 Shaterian HR, Honarmand M. Synth Commun 2011; 41 (23) 3573-3581
- 24 Maleki B. Org Prep Proced Int 2016; 48 (3) 303-318
- 25 Saha A, Payra S, Banerjee S. RSC Adv 2015; 5 (123) 101664-101671
- 26 Safaei-Ghomi J, Eshteghal F, Ghasemzadeh MA. Acta Chim Slov 2014; 61 (4) 703-708
- 27 Khurana JM, Nand B, Saluja P. Tetrahedron 2010; 66: 5637-5641
- 28 Jarrahi M, Tayebee R, Maleki B, Salimi A. RSC Adv 2021; 11 (32) 19723-19736
- 29 Pradhan K, Paul S, Das AR. Tetrahedron Lett 2013; 54 (24) 3105-3110
- 30 Khan MN, Pal S, Karamthulla S, Choudhury LH. RSC Adv 2014; 4 (8) 3732-3741
- 31 Prasanna TSR, Raju KMJ. Korean Chem Soc 2011; 55 (4) 662-665
- 32 Kiyani H, Tazari M. Res Chem Intermed 2017; 43: 6639-6650
- 33 Kiyani H, Sadat Jalali M. High Throughput Screen 2016; 19 (4) 275-282
- 34 Heravi MM, Jani BA, Derikvand F, Bamoharram FF, Oskooie HA. Catal Commun 2008; 10 (3) 272-275
- 35 Mirjalili BBF, Mehravar M, Bamoniri A, Babaei E. Org Chem Res 2021; 7 (2) 127-138
- 36 Cholayil PS, Gurusamy H, Ganapasam S. ACS Omega 2023; 8 (8) 7415-7429
- 37 Zakarieie M, Taherimehr MJ. Water Environ Nanotechnol 2024; 9 (3) 327-339
- 38a Seddon KR. J Chem Technol Biotechnol 1997; 68 (4) 351-356
- 38b Zhao H, Malhotra SV. Aldrichim Acta 2002; 35: 75-83
- 38c Swatloski RP, Holbrey JD, Rogers RD. Green Chem 2003; 5 (4) 361-363
- 38d Welton T. Chem Rev 1999; 99 (8) 2071-2084
- 38e Wasserscheid P, Keim W. Chem Int Ed 2000; 39 (21) 3772-3789
- 38f Wilkes JS. Green Chem 2002; 4 (2) 73-80
- 38g Zerth HM, Leonard NM, Mohan RS. OrgLett 2003; 5 (1) 55-57
- 38h Kumar A, Pawar SS. J Org Chem 2004; 69 (4) 1419-1420
- 38i Ledade PV, Gunjate JK, Wankhede TS, Mahmood SH, Lambat TL. Sustain Chem Environ 2025; 10: 100250
- 39 Marsh KN, Boxall JA, Lichtenthaler R. Fluid Phase Equilib 2004; 219 (1) 93-98
- 40 Ranke J, Stolte S, Störmann R, Arning J, Jastorff B. Chem Rev 2007; 107 (6) 2183-2206
- 41 Stolte S, Matzke M, Arning J. et al. Green Chem 2007; 9 (11) 1170-1179
- 42 Wang JB, Guan Y, Huo BX, Bai R, Mo LP, Zhang ZH. Mol Catal 2024; 567: 114452
- 43 Li PH, Li BL, Hu HC, Zhao XN, Zhang ZH. Catal Commun 2014; 46: 118-122
- 44 Ranu BC, Banerjee S. Org Lett 2005; 7 (14) 3049-3052
- 45 Ranu BC, Banerjee S. Lett Org Chem 2006; 3 (8) 607-609
- 46 Ranu BC, Banerjee S, Roy S, Indian J. Chem Sect B 2008; 47 (7) 1108-1112
- 47 Ambati SR, Patel JL, Gudala S. et al. Synth Commun 2020; 50 (1) 104-111
- 48 Suryawanshi R, Banjare MK, Behera K. et al. J Solution Chem 2020; 49: 715-731
- 49 Saha A, Payra S, Dutta D, Banerjee S. ChemPlusChem 2017; 82 (8) 1129-1134
- 50 Payra S, Saha A, Banerjee S. Curr Organocatal 2017; 4 (1) 4-32
- 51 Saha A, Payra S, Banerjee SJ. Appl Sol Chem Model 2016; 5 (1) 3-20
- 52 Banerjee S, Adak L, Ranu BC. Tetrahedron Lett 2012; 53 (17) 2149-2152
- 53 Ranu BC, Adak L, Banerjee S. Tetrahedron Lett 2008; 49 (31) 4613-4617
- 54 Ranu BC, Saha A, Banerjee S. Eur J Org Chem 2008; 2008: 519-523
- 55 Ranu BC, Banerjee S, Gupta J. Synth Commun 2007; 37 (17) 2869-2876
- 56 Ranu BC, Adak L, Banerjee S. Can J Chem 2007; 85 (5) 366-371
- 57 Ranu BC, Mandal T, Banerjee S, Dey SS. Aust J Chem 2007; 60 (4) 278-283
- 58 Ranu BC, Banerjee S, Jana R. Tetrahedron 2007; 63 (3) 776-782
- 59 Ranu BC, Banerjee S, Das A. Tetrahedron Lett 2006; 47 (6) 881-884
- 60 Ranu BC, Banerjee S. J Org Chem 2005; 70 (11) 4517-4519
- 61 Ranu BC, Adak L, Banerjee S. Aust J Chem 2007; 60 (5) 358-362
- 62 Heravi MM, Bakhtiari K, Zadsirjan V, Bamoharram FF, Heravi OM. Med Chem Lett 2007; 17 (15) 4262-4265