Synthesis of New Highly Functionalized Quinolines via a Novel FeIII-Catalyzed Domino aza-Michael/Aldol/Aromatization Reaction

Felix Heckmann; Mohammad M. Ibrahim; Frank Hampel; Svetlana B. Tsogoeva

doi:10.1055/s-0042-1751546

Synlett, Table of Contents

Synlett 2024; 35(09): 1007-1010
DOI: 10.1055/s-0042-1751546

cluster

Chemical Synthesis and Catalysis in Germany

Synthesis of New Highly Functionalized Quinolines via a Novel Fe^III-Catalyzed Domino aza-Michael/Aldol/Aromatization Reaction

Felix Heckmann

^aOrganic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany

,

Mohammad M. Ibrahim

^aOrganic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany

^bDepartment of Chemistry, Faculty of Science, University of Al al-Bayt, P. O. Box 130040, 25113 Al-Mafraq, Jordan

,

Frank Hampel

^aOrganic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany

,

Svetlana B. Tsogoeva ∗

^aOrganic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany

› Author Affiliations

Abstract

All articles of this category

Abstract

We report the development of a straightforward, waste-reducing, environmentally friendly, Fe^III-catalyzed domino aza-Michael/aldol/aromatization reaction in the presence of water to access high-value functionalized quinolines by using 2-aminobenzophenones and ethyl buta-2,3-dienoate as starting compounds. The tangible advantages, that is, the utilization of commercially available and/or easily accessible substrates, simplicity, mild reaction conditions, and application of water as a solvent, make this three-step domino process green and highly appealing for the direct construction of a wide variety of highly functionalized quinolines in up to 78% yield.

Key words

domino reactions - Fe catalysis - Lewis acid catalysis - quinoline synthesis - sustainability

Full Text

References

References and Notes
1 Vandekerckhove S, Tran HG, Desmet T, D’hooghe M. Bioorg. Med. Chem. Lett. 2013; 23: 4641
2 Lam K.-H, Gambari R, Lee KK.-H, Chen Y.-X, Kok SH.-L, Wong RS.-M, Lau F.-Y, Cheng C.-H, Wong W.-Y, Bian Z.-X, Chan AS.-C, Tang JC.-O, Chui C.-H. Bioorg. Med. Chem. Lett. 2014; 24: 367
3 Ratheesh M, Sindhu G, Helen A. Inflammation Res. 2013; 62: 367
4 Finley KT. Quinolines and Isoquinolines. In Kirk–Othmer Encyclopedia of Chemical Technology, Wiley Interscience: Hoboken, 2015 .
5 de La Guardia C, Stephens DE, Dang HT, Quijada M, Larionov OV, Lleonart R. Molecules 2018; 23: 672
6 Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST. Virol. J. 2005; 2: 69
7 Rolain J.-M, Colson P, Raoult D. Int. J. Antimicrob. Agents 2007; 30: 297
8 Zheng X, Wang L, Wang B, Miao K, Xiang K, Feng S, Gao L, Shen HC, Yun H. ACS Med. Chem. Lett. 2016; 7: 558
9 Talamas FX, Abbot SC, Anand S, Brameld KA, Carter DS, Chen J, Davis D, de Vicente J, Fung AD, Gong L, Harris SF, Inbar P, Labadie SS, Lee EK, Lemoine R, Le Pogam S, Leveque V, Li J, McIntosh J, Nájera I, Park J, Railkar A, Rajyaguru S, Sangi M, Schoenfeld RC, Staben LR, Tan Y, Taygerly JP, Villaseñor AG, Weller PE. J. Med. Chem. 2014; 57: 1914
10 Ezgimen M, Lai H, Mueller NH, Lee K, Cuny G, Ostrov DA, Padmanabhan R. Antiviral Res. 2012; 94: 18
11 Barbosa-Lima G, Moraes AM, Da Araújo AS, Da Silva ET, de Freitas CS, Vieira YR, Marttorelli A, Neto JC, Bozza PT, de Souza MV. N, Souza TM. L. Eur. J. Med. Chem. 2017; 127: 334
12 Vella S, Floridia M. Clin. Pharmacokinet. 1998; 34: 189
13 D’Alessandro S, Scaccabarozzi D, Signorini L, Perego F, Ilboudo DP, Ferrante P, Delbue S. Microorganisms 2020; 8: 85

14a Devaux CA, Rolain J.-M, Colson P, Raoult D. Int. J. Antimicrob. Agents 2020; 55: 105938
14b Keyaerts E, Li S, Vijgen L, Rysman E, Verbeeck J, van Ranst M, Maes P. Antimicrob. Agents Chemother. 2009; 53: 3416
14c Wang M, Cao R, Zhang L, Yang X, Liu J, Xu M, Shi Z, Hu Z, Zhong W, Xiao G. Cell Res. 2020; 30: 269

15 Ramann GA, Cowen BJ. Molecules 2016; 21: 986
16 Skraup ZH. Monatsh. Chem. 1880; 1: 316
17 Knorr L. Justus Liebigs Ann. Chem. 1886; 236: 69
18 Döbner O. Justus Liebigs Ann. Chem. 1887; 242: 265

19a Batista VF, Pinto DC. G. A, Silva AM. S. ACS Sustainable Chem. Eng. 2016; 4: 4064
19b Desai NC, Maheta AS, Rajpara KM, Joshi VV, Vaghani HV, Satodiya HM. J. Saudi Chem. Soc. 2014; 18: 963
19c Harikrishna S, Gangu KK, Robert AR, Ganja H, Kerru N, Maddila S, Jonnalagadda SB. Process Saf. Environ. Prot. 2022; 159: 911
19d Lagishetti C, Banne S, You H, Tang M, Guo J, Qi N, He Y. Org. Lett. 2019; 21: 5301
19e Mokhtar M, Alghamdi KS, Ahmed NS, Bakhotmah D, Saleh TS. J. Enzyme Inhib. Med. Chem. 2021; 36: 1454
19f Mou R.-Q, Zhao M, Lv X.-X, Zhang S.-Y, Guo D.-S. RSC Adv. 2018; 8: 9555
19g Patel A, Patel S, Mehta M, Patel Y, Patel R, Shah D, Patel D, Shah U, Patel M, Patel S, Solanki N, Bambharoliya T, Patel S, Nagani A, Patel H, Vaghasiya J, Shah H, Prajapati B, Rathod M, Bhimani B, Patel R, Bhavsar V, Rakholiya B, Patel M, Patel P. Green Chem. Lett. Rev. 2022; 15: 337
19h Patel DB, Rajani DP, Rajani SD, Patel HD. J. Heterocycl. Chem. 2020; 57: 1524
19i Reddy LV, Nallapati SB, Beevi SS, Mangamoori LN, Mukkanti K, Pal S. J. Braz. Chem. Soc. 2011; 22: 1742
19j Reddy RS, Zheng S, Lagishetti C, You H, He Y. RSC Adv. 2016; 6: 68199
19k Santhosh Reddy R, Lagishetti C, Kiran IN. C, You H, He Y. Org. Lett. 2016; 18: 3818
19l Singh HK, Kamal A, Maury SK, Kushwaha AK, Srivastava V, Singh S. Org. Biomol. Chem. 2023; 21: 4854
19m Tasqeeruddin S, Asiri Y, Alsherhri JA. Lett. Org. Chem. 2020; 17: 157
19n Yadav P, Bhalla A. ChemistrySelect 2022; 7: e202201721
19o You H, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang X, Guo J, Wang C, He Y. J. Org. Chem. 2018; 83: 4119

20a Rueping M, Dufour J, Schoepke FR. Green Chem. 2011; 13: 1084
20b Marqués-López E, Herrera RP, Christmann M. Nat. Prod. Rep. 2010; 27: 1138
20c de Figueiredo RM, Christmann M. Eur. J. Org. Chem. 2007; 2575
20d Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167

21a Albrecht Ł, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2011; 50: 8492
21b Chapman C, Frost C. Synthesis 2007; 1
21c Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
21d Guo H.-C, Ma J.-A. Angew. Chem. Int. Ed. 2006; 45: 354
21e Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
21f Pellissier H. Tetrahedron 2006; 62: 1619
21g Pellissier H. Tetrahedron 2006; 62: 2143
21h Tietze LF. Chem. Rev. 1996; 96: 115
21i Tietze L.-F, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
21j Vaxelaire C, Winter P, Christmann M. Angew. Chem. Int. Ed. 2011; 50: 3605

22a Held FE, Guryev AA, Fröhlich T, Hampel F, Kahnt A, Hutterer C, Steingruber M, Bahsi H, von Bojničić-Kninski C, Mattes DS, Foertsch TC, Nesterov-Mueller A, Marschall M, Tsogoeva SB. Nat. Commun. 2017; 8: 15071
22b Grau BW, Bönisch S, Neuhauser A, Hampel F, Görling A, Tsogoeva SB. ChemCatChem 2019; 11: 3982
22c Grau D, Grau BW, Hampel F, Tsogoeva SB. Chem. Eur. J. 2018; 24: 6551

Supplementary Material

Supporting Information