Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolo­coumarins

Thomas D. Balalas; Maria G. Kanelli; Catherine Gabriel; Eleni Pontiki; Dimitra J. Hadjipavlou-Litina; Konstantinos E. Litinas

doi:10.1055/s-0037-1610793

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(12): 2894-2806
DOI: 10.1055/s-0037-1610793

paper

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

Thomas D. Balalas

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

,

Maria G. Kanelli

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

,

Catherine Gabriel

^bCenter for Research of the Structure of Matter, Magnetic Resonance Laboratory, Department of Chemical Engineering, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

,

Eleni Pontiki

^cDepartment of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

,

Dimitra J. Hadjipavlou-Litina

^cDepartment of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

,

Konstantinos E. Litinas ∗

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

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Abstract

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Abstract

1-Aryl-2-methyl- or 3-methylchromeno[4,3-b]pyrrol-4(1H)-ones have been synthesized in excellent yields by the Pd-catalyzed intramolecular aza-Wacker-type cyclization of 3-allyl-4-arylaminocoumarins or C–H insertion/oxidative cyclization of N-allyl-N-aryl-4-aminocoumarins, respectively, in the presence of Cu(OAc)₂ in acetic acid under heating. The starting allylcoumarins have been prepared by the allylation of 4-arylaminocoumarins with allyl bromide in CH₃CN in the presence of Cs₂CO₃ at room temperature. Preliminary biological tests indicated interesting antioxidant activity and significant levels of inhibition of soybean lipoxygenase.

Key words

[3,4]-fused pyrrolocoumarins - Pd-catalyzed aza-Wacker oxidative cyclization - copper acetate - 3-allyl-4-arylaminocoumarins - N-allyl-N-aryl-4-aminocoumarins

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Referenzen

References

1a Yu DL, Suzuki M, Xie L, Morris-Natsche SL, Lee KH. Med. Res. Rev. 2003; 23: 322
1b Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Curr. Pharm. Des. 2004; 10: 3813
1c Lacy A, O’Kennedy R. Curr. Pharm. Des. 2004; 10: 3797
1d Medina FG, Marrero JG, Alonso MM, González MC, Córdova-Guerrero I, García AG. T, Osegueda-Robles S. Nat. Prod. Rep. 2015; 32: 1472
1e Kubrak T, Podgorski R, Stompor M. Eur. J. Clin. Exp. Med. 2017; 15: 169
1f Li H, Yao Y, Li L. J. Pharm. Pharmacol. 2017; 69: 1253
1g Salehian F, Nadri H, Jalili-Baleh L, Youseftabar-Miri L, Abbas Bukhari SN, Foroumadi A, Küçükkilinç TT, Sharifzadeh M, Khoobi M. Eur. J. Med. Chem. 2021; 212: 113034

2a Guiotto A, Chilin A, Manzini P, Dall’Acqua F, Bordin F, Rodighiero P. Farmaco 1995; 50: 479
2b Reddy MV. R, Rao MR, Rhodes D, Hansen MS. T, Rubins K, Bushman FD, Venkateswarlu Y, Faulkner DJ. J. Med. Chem. 1999; 42: 1901
2c Boger DL, Soenen DR, Boyce CW, Hedrick MP, Jin Q. J. Org. Chem. 2000; 65: 2479
2d Kontogiorgis C, Litinas KE, Makri A, Nicolaides DN, Vronteli A, Hadjipavlou-Litina DJ, Pontiki E, Siohou A. J. Enzyme Inhib. Med. Chem. 2008; 23: 43
2e Neagoie C, Vedrenne E, Buron F, Merour JY, Rosca S, Bourg S, Lozach O, Meijer L, Baldeyrou B, Lansiaux A, Routier S. Eur. J. Med. Chem. 2012; 49: 379
2f Vronteli A, Hadjipavlou-Litina DJ, Konstantinidou M, Litinas KE. ARKIVOC 2015; (iii): 111
2g Mukherjee S, Hazra S, Chowdhury S, Sarkar S, Chattopadhyay K, Pramanik A. J. Photochem. Photobiol., A 2018; 364: 635

For a review see:

3a Bailly C. Mar. Drugs 2015; 13: 1105
3b Imbri D, Tauber J, Opatz T. Mar. Drugs 2014; 12: 6142
3c Zhang N, Wang D, Zhu Y, Wang J, Lin H. Asian Pac. J. Cancer Prev. 2014; 15: 9915
3d Zhou X, Liu J, Yang B, Lin X, Yang X.-W, Liu Y. Curr. Med. Chem. 2013; 20: 953
3e Fukuda T, Ishibashi F, Iwao M. Heterocycles 2011; 83: 491
3f Chittchang M, Batsomboon P, Ruchirawat S, Ploypradith P. ChemMedChem 2009; 4: 457
3g Fan H, Peng J, Hamann MT, Hu JH. Chem. Rev. 2008; 108: 264

4a Thakur A, Thakur M, Khadikar P. Bioorg. Med. Chem. 2003; 11: 5203
4b Colotta V, Cecchi L, Melani F, Filacchioni G, Martini C, Giannaccini G, Lucacchini A. J. Med. Chem. 1990; 33: 2646

5 Dakshanamurthy S, Kim M, Brown ML, Byers SW. Bioorg. Med. Chem. Lett. 2007; 17: 4551
6 Vidadala SR, Waldmann H. Tetrahedron Lett. 2015; 56: 3358

Selected examples for the synthesis of ningalin B:

7a Bullington JL, Wolff RR, Jackson PF. J. Org. Chem. 2002; 67: 9439
7b Axford LC, Holden KE, Hasse K, Banwell MG, Steglich W, Wagler J, Willis AC. Aust. J. Chem. 2008; 61: 80
7c Hasse K, Willis AC, Banwell MG. Aust. J. Chem. 2009; 62: 683

8 Bashiardes G, Safir I, Barbot F, Laduranty J. Tetrahedron Lett. 2003; 44: 8417
9 Yu H, Zhang L, Yang Z, Li Z, Zhao Y, Xiao Y, Guo H. J. Org. Chem. 2013; 78: 8427
10 Khan MA, De Brito Morley ML. J. Heterocycl. Chem. 1978; 15: 1399

11a Alberola Á, Álvaro R, Andrés JM, Calvo B, González A. Synthesis 1994; 279
11b Somman SS, Thaker TH, Rajput RA. Chem. Heterocycl. Comp. 2011; 46: 1514
11c Alberola A, Alvaro R, González-Ortega A, Sadaba ML, Sanudo MC. Tetrahedron 1999; 55: 13211

12a Alberola A, Calvo L, González-Ortega A, Encabo AP, Sanudo MC. Synthesis 2001; 1941
12b Liao Y.-X, Kuo P.-Y, Yang D.-Y. Tetrahedron Lett. 2003; 44: 1599
12c Lin C.-H, Yang D.-Y. Org. Lett. 2013; 15: 2802

13a Saha M, Pradhan K, Das AR. RSC Adv. 2016; 6: 55033
13b Yang X, Jing L, Chen Z. Chem. Heterocycl. Comp. 2018; 54: 1065
13c Yahyavi H, Heravi MM, Mahdavi M, Foroumadi A. Tetrahedron Lett. 2018; 59: 94

14a Chen Z.-W, Hou J.-B, Dai Z.-R, Yang X.-F. Chin. Chem. Lett. 2016; 27: 1622
14b Padilha G, Iglesias BA, Back DF, Kaufman TS, Silveira CC. ChemistrySelect 2017; 2: 1297
14c Pandya MK, Chhasatia MR, Vala ND, Parekh TJ. J. Drug Delivery Ther. 2019; 9: 32

15 Majumdar KC, Chattopadhyay B. Synthesis 2008; 921

16a Majumdar KC, De N, Roy B. Synthesis 2010; 4207
16b Ngo TN, Akrawi OA, Dang TT, Villinger A, Langer P. Tetrahedron Lett. 2015; 56: 86
16c Chen L, Xu M.-H. Adv. Synth. Catal. 2009; 351: 2005
16d Peng S, Wang L, Huang J, Sun S, Guo H, Wang J. Adv. Synth. Catal. 2013; 355: 2550

Pd-Catalyzed synthesis of pyrroles:

17a Wang Z, Chen W, Luo H, He C, Zhang G, Yu Y. Synthesis 2020; 52: 1659
17b Santhini PV, Nimisha G, John J, Suresh E, Varma RL, Radhakrishnan KV. Chem. Commun. 2017; 53: 1848
17c Torres GM, Quesnel JS, Bijou D, Arndsen BA. J. Am. Chem. Soc. 2016; 138: 7315
17d Yu Y, Mang Z, Yang W, Li H, Wang W. Catalysts 2016; 6: 169
17e Zheng J, Huang L, Huang C, Wu W, Jiang H. J. Org. Chem. 2015; 80: 1235
17f Zhao M.-N, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Org. Lett. 2014; 16: 608
17g Trost BM, Lumb J.-P, Azzarelli JM. J. Am. Chem. Soc. 2011; 133: 740

Selective examples for the Pd-catalyzed synthesis of indoles:

18a Thombal RS, Lee YR. Org. Lett. 2020; 22: 3397
18b Chang Z, Ma T, Zhang Y, Dong Z, Zhao H, Zhao D. Molecules 2020; 25: 1233
18c Savvidou A, Tzaras DI, Koutoulogenis GS, Theodorou A, Kokotos CG. Eur. J. Org. Chem. 2019; 3890
18d Ning X.-S, Wang M.-M, Qu J.-P, Kang Y.-B. J. Org. Chem. 2018; 83: 13523
18e Zhou Q, Zhang Z, Zhou Y, Li S, Zhang Y, Wang J. J. Org. Chem. 2017; 82: 48
18f Yu S, Qi L, Hu K, Gong J, Cheng T, Wang Q, Chen J, Wu H. J. Org. Chem. 2017; 82: 3631
18g Nallagonda R, Rehan M, Ghorai P. Org. Lett. 2014; 16: 4786
18h Nanjo T, Tsukano C, Takemoto Y. Org. Lett. 2012; 14: 4270
18i Shi Z, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 92
18j Neumann JJ, Rakshit S, Droge T, Wurtz S, Glorius F. Chem. Eur. J. 2011; 17: 7298
18k Wurtz S, Rakshit S, Neumann JJ, Droge T, Glorius F. Angew. Chem. Int. Ed. 2008; 47: 7230

Selective examples for the intramolecular aza-Wacker reaction:

19a Thomas AA, Nagamallqa S, Sathyamoorthi S. Chem. Sci. 2020; 11: 8073
19b Kou X, Shao Q, Ye C, Yang G, Zhang W. J. Am. Chem. Soc. 2018; 140: 7587
19c Bao X, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2018; 57: 1995
19d Gu Q.-S, Yang D. Angew. Chem. Int. Ed. 2017; 56: 5886
19e He Y.-P, Wu H, Xu L, Su Y.-L, Gong L.-Z. Org. Chem. Front. 2014; 1: 473
19f Lu Z, Stahl SS. Org. Lett. 2012; 14: 1234
19g McDonald RI, White PB, Weinstein AB, Tam CP, Stahl SS. Org. Lett. 2011; 13: 2830
19h Zhang Z, Tan J, Wang Z. Org. Lett. 2008; 10: 173
19i Minatti A, Muniz K. Chem. Soc. Rev. 2007; 36: 1142

20 Balalas T, Abdul-Sada A, Hadjipavlou-Litina DJ, Litinas KE. Synthesis 2017; 49: 2575

21a Balalas TD, Theologis AK, Mazaraki K, Gabriel C, Pontiki E, Hadjipavlou-Litina DJ, Litinas KE. ARKIVOC 2020; (vi): 126
21b Balalas TD, Kallitsakis MG, Fotopoulos I, Hadjipavlou-Litina DJ, Litinas KE. ARKIVOC 2019; (vi): 237
21c Vlachou E.-EN, Gabriel C, Litinas KE. J. Heterocycl. Chem. 2019; 56: 99
21d Balalas TD, Stratidis G, Papatheodorou D, Vlachou E.-EN, Gabriel C, Hadjipavlou-Litina DJ, Litinas KE. SynOpen 2018; 2: 105
21e Vlachou E.-EN, Armatas GS, Litinas KE. J. Heterocycl. Chem. 2017; 54: 2447
21f Symeonidis TS, Hadjipavlou-Litina DJ, Litinas KE. J. Heterocycl. Chem. 2014; 51: 642
21g Symeonidis TS, Litinas KE. Tetrahedron Lett. 2013; 54: 6517
21h Symeonidis TS, Lykakis IN, Litinas KE. Tetrahedron 2013; 69: 4612
21i Litinas KE, Mangos A, Nikkou TE, Hadjipavlou-Litina DJ. J. Enzyme Inhib. Med. Chem. 2011; 26: 805

22 Ivanov CI, Karagiosov SA, Simeonov MF. Liebigs Ann. Chem. 1992; 203
23 Sosa DO, Almaraz K, Amezquita-Valencia M. Eur. J. Org. Chem. 2019; 4682

24a Jayaprakash RY, Chakravarthulla V. J. Heterocycl. Chem. 2015; 52: 1014
24b Majumdar KC, Biswas A, Mukkopadhyay PP. Can. J. Chem. 2005; 83: 2046
24c Majumdar KC, Basu PK, Roy B. Synth. Commun. 2003; 33: 3621
24d Chattopadhyay SK, Maity S, Panja S. Tetrahedron Lett. 2002; 43: 7781

25 Balabani A, Hadjipavlou-Litina DJ, Litinas KE, Mainou M, Tsironi C.-C, Vronteli A. Eur. J. Med. Chem. 2011; 46: 5894

Zusatzmaterial

Supporting Information

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolo­coumarins

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins