Synthesis, Table of Contents Synthesis 2024; 56(14): 2277-2283DOI: 10.1055/s-0043-1763690 paper One-Pot N-α-C(sp3)–H Bond Functionalisation Cascade for the Synthesis of Polysubstituted Imidazoles Authors Author Affiliations Vikas D. Kadu ∗ a School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur 413255, Maharashtra, India Naga Chandradudu Sankala b Department of Chemistry, College of Engineering, Rayalseema University, Kurnool 518002, Andhra Pradesh, India Mahesh G. Hublikar a School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur 413255, Maharashtra, India Shahaji I. Bansode a School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur 413255, Maharashtra, India Raghunath B. Bhosale a School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur 413255, Maharashtra, India Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A one-pot eco-friendly oxidative N-α-C(sp3)–H bond functionalisation of arylmethylamines for the synthesis of tetrasubstituted imidazoles is demonstrated. The substrate scope of these amines has been well-explored with different substrates, such as 1,2-diketones, an α-hydroxy ketone and phenylacetophenone. In the presence of FeCl3 catalyst and green oxidant O2, the easily accessible substrates afforded tetrasubstituted imidazoles in up to 94% yield. Key words Key wordsimidazoles - iron catalysis - oxidative coupling - N-α-C(sp3)–H functionalisation - one-pot reaction Full Text References References 1 Kabi AK, Sravani S, Gujjarappa R, Garg A, Vodnala N, Tyagi U, Kaldhi D, Velayutham R, Gupta S, Malakar CC. In Nanostructured Biomaterials. Materials Horizons: From Nature to Nanomaterials . Swain BP. Springer; Singapore: 2022: 79 2 Hublikar M, Kadu V, Dublad JK, Raut D, Shirame S, Makam P, Bhosale R. Arch. Pharm. 2020; 353: 2000003 3 Raut DG, Patil SB, Choudhari PB, Kadu VD, Lawand AS, Hublikar MG, Bhosale RB. Curr. Chem. Biol. 2020; 14: 58 4 Raut DG, Patil SB, Kadu VD, Hublikar MG, Bhosale RB. Anti-Cancer Agents Med. Chem. 2018; 18: 2117 5 Raut DG, Bhosale RB, Lawand AS, Hublikar MG, Kadu VD, Patil SB. Recent Adv. Inflammation Allergy Drug Discovery 2022; 16: 19 6 De Luca L. Curr. Med. Chem. 2006; 13: 1 7 Tolomeu HV, Fraga CA. M. Molecules 2023; 28: 838 8 Sharma P, Larosa C, Antwi J, Govindarajan R, Werbovetz KA. Molecules 2021; 26: 4213 9 Zhang L, Peng X.-M, Damu GL. V, Geng R.-X, Zhou C.-H. Med. Res. Rev. 2014; 34: 340 10 Bhowmick NA, Chytil A, Plieth D, Gorska AE, Dumont N, Shappell S, Washington MK, Neilson EG, Moses HL. Science 2004; 303: 848 11 Riduan SN, Zhang Y. Chem. Soc. Rev. 2013; 42: 9055 12 Rani N, Sharma A, Gupta GK, Singh R. Mini-Rev. Med. Chem. 2013; 13: 1626 13 Castelli MV, Butassi E, Monteiro MC, Svetaz LA, Vicente F, Zacchino SA. Expert Opin. Ther. Pat. 2014; 24: 323 14 Gaba M, Mohan C. Med. Chem. Res. 2016; 25: 173 15 Grimmett MR. Adv. Heterocycl. Chem. 1981; 27: 241 16 Sundberg RJ. Chem. Rev. 1974; 74: 471 17 Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A. Bioorg. Med. Chem. Lett. 1999; 9: 1023 18 Gupta P, Hameed S, Jain R. Eur. J. Med. Chem. 2004; 39: 805 19 Uçucu Ü, Karaburun NG, Işikdag I. Farmaco 2001; 56: 285 20 Rocha JA, Andrade IM, Véras LM. C, Quelemes PV, Lima DF, Soares MJ. S, Pinto PL. S, Mayo SJ, Ivanova G, Rangel M, Correia M, Mafud AC, Mascarenhas YP, Delerue-Matos C, de Moraes J, Eaton P, Leite JR. S. A. Phytother. Res. 2017; 31: 624 21 Silva VG, Silva RO, Damasceno SR. B, Carvalho NS, Prudeîncio RS, Aragão KS, Guimarães MA, Campos SA, Véras LM. C, Godejohann M, Leite JR. S. A, Barbosa AL. R, Medeiros JV. R. J. Nat. Prod. 2013; 76: 1071 22 Wang L, Woods KW, Li Q, Barr KJ, McCroskey RW, Hannick SM, Gherke L, Credo RB, Hui Y.-H, Marsh K, Warner R, Lee JY, Zielinski-Mozng N, Frost D, Rosenberg SH, Sham HL. J. Med. Chem. 2002; 45: 1697 23 Evans LE, Cheeseman MD, Yahya N, Jones K. PLoS One 2015; 10: 1 24 Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW. Org. Lett. 2004; 6: 1453 25 Laufer SA, Zimmermann W, Ruff KJ. J. Med. Chem. 2004; 47: 6311 26 Lee JC, Laydon JT, McDonnell PC, Gallagher TF, Kumar S, Green D, McNulty D, Blumenthal MJ, Keys JR, Land vatter SW, Strickler JE, McLaughlin MM, Siemens IR, Fisher SM, Livi GP, White JR, Adams JL, Young PR. Nature 1994; 372: 739 27 Molina P, Tárraga A, Otón F. Org. Biomol. Chem. 2012; 10: 1711 28 Gurjar S, Sharma SK, Sharma A, Ratnani S. Appl. Surf. Sci. Adv. 2021; 6: 100170 29 Cao Y, Zhang R, Cheng T, Guo J, Xian M, Liu H. Appl. Microbiol. Biotechnol. 2017; 101: 521 30 Saheed IO, Azeez SO, Suah FB. M. Carbohydr. Polym. 2022; 298: 120138 31 Meng X, Wang H.-N, Song S.-Y, Zhang H.-J. Chem. Soc. Rev. 2017; 46: 464 32 Ngan VT. T, Chiou P.-Y, Ilhami FB, Bayle EA, Shieh Y.-T, Chuang W.-T, Chen J.-K, Lai J.-Y, Cheng C.-C. Pharmaceutics 2023; 15: 354 33 Zhang F.-M, Dong L.-Z, Qin J.-S, Guan W, Liu J, Li S.-L, Lu M, Lan Y.-Q, Su Z.-M, Zhou H.-C. J. Am. Chem. Soc. 2017; 139: 6183 34 Guo J, Yang Q, Meng Q.-W, Lau CH, Ge Q. ACS Appl. Mater. Interfaces 2021; 13: 6710 35 Li BS, Wen R, Xue S, Shi L, Tang Z, Wang Z, Tang BZ. Mater. Chem. Front. 2017; 1: 646 36 Liu M, Jiang Y, Liu D, Wang J, Ren Z, Russell TP, Liu Y. ACS Energy Lett. 2021; 6: 3228 37 Park S, Kwon O.-H, Kim S, Park S, Choi M.-G, Cha M, Park SY, Jang D.-J. J. Am. Chem. Soc. 2005; 127: 10070 38 Li F.-G, Liu C, Yuan D, Dai F, Wang R, Wang Z, Lu X, Sun D. CCS Chem. 2022; 4: 832 39 Ali R, Dwivedi SK, Mishra H, Misra A. Dyes Pigm. 2020; 175: 108163 40 Zhang Q, Luo L, Xu H, Hu Z, Brommesson C, Wu J, Sun Z, Tian Y, Uvdal K. New J. Chem. 2016; 40: 3456 41 Sahoo A, Deb S, Das S, Baitalik S. Dyes Pigm. 2023; 218: 111425 42 Pavan G, Morgan L, Demitri N, Alberoni C, Scattolin T, Aliprandi A. Chem. Eur. J. 2023; 29: e202301912 43 Felber T, Schaefer T, Herrmann H. J. Phys. Chem. A 2020; 124: 10029 44 Huang H, Ji X, Wu W, Jiang H. Adv. Synth. Catal. 2013; 355: 170 45 Kadu VD, Mali GA, Khadul SP, Kothe GJ. RSC Adv. 2021; 11: 21955 46 Cao J, Zhou X, Ma H, Shi C, Huang G. RSC Adv. 2016; 6: 57232 47 Salfeena CT. F, Jalaja R, Davis R, Suresh E, Somappa SB. ACS Omega 2018; 3: 8074 48 Yang Z, Zhang J, Hu L, Li A, Li L, Liu K, Yang T, Zhou C. J. Org. Chem. 2020; 85: 5952 49 Zhang B, Wan C, Wang Q, Zhang S, Zha Z, Wang Z. Acta Chim. Sin. 2012; 70: 2408 50 Sadeghi B, Mirjalili BB. F, Hashemi MM. Tetrahedron Lett. 2008; 49: 2575 51 Balalaie S, Arabanian A. Green Chem. 2000; 2: 274 52 Heravi MM, Derikvand F, Bamoharram FF. J. Mol. Catal. A: Chem. 2007; 263: 112 53 Chen X, Wang Z, Huang H, Deng GJ. Adv. Synth. Catal. 2018; 360: 4017 54 Donohoe TJ, Kabeshov MA, Rathi AH, Smith IE. D. Org. Biomol. Chem. 2012; 10: 1093 55 Sarkar R, Mukhopadhyay C. Eur. J. Org. Chem. 2015; 1246 56 Claiborne CF, Liverton NJ, Nguyen KT. Tetrahedron Lett. 1998; 39: 8939 57 Wang M, Li L, Lu J, Luo N, Zhang X, Wang F. Green Chem. 2017; 19: 5172 58 Samanta S, Roy D, Khamarui S, Maiti DK. Chem. Commun. 2014; 50: 2477 59 Kadu VD, Khadul SP, Kothe GJ, Mali GA. Asian J. Org. Chem. 2022; 11: e202200162 60 Adhikary S, Majumder L, Pakrashy S, Srinath R, Mukherjee K, Mandal C, Banerji B. ACS Omega 2020; 5: 14394 61 Gopalaiah K. Chem. Rev. 2013; 113: 3248 62 Darwish M, Wills M. Catal. Sci. Technol. 2012; 2: 243 63 Junge K, Schröder K, Beller M. Chem. Commun. 2011; 47: 4849 64 Correa A, García Mancheño O, Bolm C. Chem. Soc. Rev. 2008; 37: 1108 65 Bolm C. Nat. Chem. 2009; 1: 420 66 Bauer EB. Curr. Org. Chem. 2008; 12: 1341 67 Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217 68 Fürstner A. ACS Cent. Sci. 2016; 2: 778 69 Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068 70 Kadu VD. ChemistrySelect 2022; 7: e202104028 71 Tashrifi Z, Khanaposhtani MM, Larijani B, Mahdavi M. Tetrahedron 2021; 84: 131990 72 Alanthadka A, Elango SD, Thangavel P, Subbiah N, Vellaisamy S, Chockalingam UM. Catal. Commun. 2019; 125: 26 73 Kadu VD, Patil AA, Shendage PR. J. Mol. Struct. 2022; 1267: 133502 74 Kadu VD, Chandrudu SN, Hublikar MG, Raut DG, Bhosale RB. RSC Adv. 2020; 10: 23254 75 Zhang Y, Zhang T, Das S. Chem 2022; 8: 3175 76 Gunasekaran N. Adv. Synth. Catal. 2015; 357: 1990 77 Pavithra T, Devi ES, Maheswari CU. Asian J. Org. Chem. 2021; 10: 1861 78 Sterckx H, Morel B, Maes BU. W. Angew. Chem. Int. Ed. 2019; 58: 7946 79 Zhang L.-Y, Wang N.-X, Lucan D, Cheung W, Xing Y. Chem. Eur. J. 2023; 29: e202301700 80 Gopalaiah K, Chandrudu SN. RSC Adv. 2015; 5: 5015 81 Kadu VD, Gund MS, Godage AS. ChemistrySelect 2021; 6: 11954 82 Naróg D, Lechowicz U, Pietryga T, Sobkowiak A. J. Mol. Catal. A: Chem. 2004; 212: 25 83 Rosenau T, Hofinger A, Potthast A, Kosma P. Org. Lett. 2004; 6: 541 84 Yi X, Yi X, Lei S, Liu W, Che F, Yu C, Liu X, Wang Z, Zhou X, Zhang Y. Org. Lett. 2020; 22: 4583 85 Zhang E, Tian H, Xu S, Yu X, Xu Q. Org. Lett. 2013; 15: 2704 Supplementary Material Supplementary Material Supporting Information (PDF)
