A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones

H. Sebastián Steingruber; Pamela Mendioroz; M. Julia Castro; María A. Volpe; Darío C. Gerbino

doi:10.1055/s-0042-1751371

Synthesis, Table of Contents

Synthesis 2023; 55(04): 692-706
DOI: 10.1055/s-0042-1751371

paper

A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones

H. Sebastián Steingruber

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

,

Pamela Mendioroz

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

,

M. Julia Castro

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

,

María A. Volpe

^bPlanta Piloto de Ingeniería Química (PLAPIQUI-CONICET), Camino La Carrindanga Km 7, 8000 Bahía Blanca, Argentina

,

Darío C. Gerbino∗

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Hans-Günther Schmalz on the occasion of his 65^th birthday

Abstract

In order to develop an efficient, rapid, and modular cascade strategy for the direct synthesis of acridones, palladium supported on sulfated alumina and microwave activation are employed. Multifunctional heterogeneous palladium catalysts were prepared in order to carry out the sequential annulation via a Buchwald–Hartwig amination followed by an intramolecular annulation in a one-pot process. This new protocol represents the first report on a catalytic tandem synthesis of acridone derivatives from commercially available starting materials, under ligand-free conditions. The scope of the present methodology is extended to the generation of a library of functionalized acridones, showing high functional group compatibility, in moderate to excellent yields. The applicability of this novel transformation was demonstrated by the concise total synthesis of the natural product arborinine.

Key words

acridones - tandem reaction - palladium catalysis - sulfated alumina - synthetic methodology

Full Text

References

References
1 Kumar R, Sharma S, Prasad D. In Key Heterocycle Cores for Designing Multitargeting Molecules, Chap. 3. Silakari O. Elsevier; Amsterdam: 2018

2a Miglbauer E, Demitri N, Himmelsbach M, Monkowius U, Sariciftci NS, Głowacki ED, Oppelt KT. ChemistrySelect 2016; 1: 6349
2b Hamzehpoor E, Ruchlin C, Tao Y, Ramos-Sanchez JE, Titi HM, Cosa G, Perepichka DF. J. Phys. Chem. Lett. 2021; 12: 6431

3a Gao H, Zhang G. Eur. J. Org. Chem. 2020; 5455
3b Pereira RC, Pontinha AD. R, Pineiro M, Seixas de Melo JS. Dyes Pigm. 2019; 166: 203
3c Chan YC, Li CY, Lai CW, Wu MW, Tseng HJ, Chang CC. Appl. Sci. 2020; 10: 8708
3d Singh P, Kumar A, Kaur S, Singh A, Gupta M, Kaur G. Med. Chem. Commun. 2016; 7: 632
3e Faller T, Hutton K, Okafo G, Gribble A, Camilleri P, Games DE. Chem. Commun. 1997; 1529

4a Zheng Z, Dian L, Yuan Y, Zhang-Negrerie D, Du Y, Zhao K. J. Org. Chem. 2014; 79: 7451
4b Zhou W, Yang Y, Liu Y, Deng GJ. Green Chem. 2013; 15: 76
4c Yu J, Yang H, Jiang Y, Fu H. Chem. Eur. J. 2013; 19: 4271
4d Li XA, Wang HL, Yang SD. Org. Lett. 2013; 15: 1794
4e MacNeil SL, Gray M, Gusev DG, Briggs LE, Snieckus V. J. Org. Chem. 2008; 73: 9710

5a Huang PC, Parthasarathy K, Cheng CH. Chem. Eur. J. 2013; 19: 460
5b Zhou W, Liu Y, Yang Y, Deng GJ. Chem. Commun. 2012; 48: 10678
5c Wei WT, Sheng JF, Miao H, Luo X, Song XH, Yan M, Zou Y. Adv. Synth. Catal. 2018; 360: 2101

6 Wen J, Tang S, Zhang F, Shi R, Lei A. Org. Lett. 2017; 19: 94
7 Wu H, Zhang Z, Liu Q, Liu T, Ma N, Zhang G. Org. Lett. 2018; 20: 2897
8 Zhao J, Larock RC. J. Org. Chem. 2007; 72: 583
9 Pang X, Lou Z, Li M, Wen L, Chen C. Eur. J. Org. Chem. 2015; 3361
10 Jiang CY, Xie H, Huang ZJ, Liang JY, Huang YX, Liang QP, Zeng JY, Zhou B, Zhang SS, Shu B. Org. Biomol. Chem. 2021; 19: 8487

11a Wu H, Ma N, Song M, Zhang G. Chin. Chem. Lett. 2020; 31: 1580
11b Janke J, Villinger A, Ehlers P, Langer P. Synlett 2019; 30: 817
11c Xiao L, Liu G, Li Z, Ren P, Ren L, Kong J. Chin. J. Org. Chem. 2020; 40: 2988
11d Zhang LJ, Yang W, Hu Z, Zhang XM, Xu X. Adv. Synth. Catal. 2020; 362: 2379

12 Climent MJ, Corma A, Iborra S, Sabater MJ. ACS Catal. 2014; 4: 870

13a Climent MJ, Corma A, Iborra S. Chem. Rev. 2011; 111: 1072
13b Climent MJ, Corma A, Iborra S. RSC Adv. 2012; 2: 16

14a Steingruber HS, Mendioroz P, Diez AS, Gerbino DC. Synthesis 2020; 52: 619
14b Steingruber HS, Mendioroz P, Volpe MA, Gerbino DC. Synthesis 2021; 53: 4048

15a Guram AS, Buchwald SL. J. Am. Chem. Soc. 1994; 116: 7901
15b Paul F, Patt J, Hartwig JF. J. Am. Chem. Soc. 1994; 116: 5969
15c Dorel R, Grugel CP, Haydl AM. Angew. Chem. Int. Ed. 2019; 58: 17118
15d Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564

16a Wakaki T, Togo T, Yoshidome D, Kuninobu Y, Kanai M. ACS Catal. 2018; 8: 3123
16b Tetsuya S, Tomoaki I, Masahiro M, Masakatsu N. Chem. Lett. 1996; 25: 823

17 López-Aguado C, Paniagua M, Melero JA, Iglesias J, Juárez P, López Granados M, Morales G. Catalysis 2020; 10: 678
18 Neyertz C, Volpe M, Gigola C. Appl. Catal., A 2004; 277: 137
19 Casoni AI, Hoch PM, Volpe MA, Gutierrez VS. J. Clean. Prod. 2018; 178: 237
20 Mao Z, Gu H, Lin X. Catalysts 2021; 11: 1
21 Liu J, He F, Gunn TM, Zhao D, Roberts CB. Langmuir 2009; 25: 7116
22 Piccolo L. Catal. Today 2021; 373: 80

23a Banerjee SK, Chakravarti D, Chakravarti RN, Fales HM, Klayman DL. Tetrahedron 1961; 16: 251
23b Muriithi MW, Abraham WR, Addae-Kyereme J, Scowen I, Croft SL, Gitu PM, Kendrick H, Njagi EN. M, Wright CW. J. Nat. Prod. 2002; 65: 956
23c Waffo AF. K, Coombes PH, Crouch NR, Mulholland DA, El Amin SM, Smith PJ. Phytochemistry 2007; 68: 663

24a Hughes G, Ritchie E. Aust. J. Chem. 1951; 4: 423
24b Hughes G, Neill K, Ritchie E. Aust. J. Chem. 1950; 3: 497
24c Pal C, Kundu MK, Bandyopadhyay U, Adhikari S. Bioorg. Med. Chem. Lett. 2011; 21: 3563
24d Bera SS, Sk MR, Maji MS. Chem. Eur. J. 2019; 25: 1806

25 Yan MC, Tu Z, Lin C, Ko S, Hsu J, Yao CF. J. Org. Chem. 2004; 69: 1565

26a Song J, Ding K, Sun W, Wang S, Sun H, Xiao K, Liu C. Tetrahedron Lett. 2018; 59: 2889
26b Álvarez-Bercedo P, Flores-Gaspar A, Correa A, Martin R. J. Am. Chem. Soc. 2010; 132: 466

27 Rahim K, Farhadi M, Forough M, Hajizadeh S. J. Nanostruct. 2018; 8: 47
28 Amarego WL. F. Purification of Laboratory Chemicals, 8th ed. Butterworth-Heinemann; Oxford: 2017
29 Garcia EA, Rueda EH, Rouco AJ. Appl. Catal., A 2001; 210: 363
30 Wei WT, Sheng JF, Miao H, Luo X, Song XH, Yan M, Zou Y. Adv. Synth. Catal. 2018; 360: 2101

31a Knapp W. Monatsh. Chem. 1937; 70: 251
31b Xiong Z, Zhang X, Li Y, Peng X, Fu J, Guo J, Xie F, Jiang C, Lin B, Liu Y, Cheng M. Org. Biomol. Chem. 2018; 16: 7361

32 Bongui JB, Elomri A, Seguin E, Tillequin F, Pfeiffer B, Renard P, Pierre A, Atassi G. Chem. Pharm. Bull. 2001; 49: 1077
33 Ghosh P, Ganguly B, Das S. Appl. Organomet. Chem. 2018; 32: e4173
34 Hayashi K, Matsumoto A, Hirata S. Chem. Commun. 2021; 57: 1738
35 Wu H, Zhang Z, Liu Q, Liu T, Ma N, Zhang G. Org. Lett. 2018; 20: 2897
36 Parveen M, Aslam A, Nami SA. A, Malla AM, Alam M, Lee DU, Rehman S, Silva PS. P, Silva MR. J. Photochem. Photobiol., B 2016; 161: 304
37 Kancharla P, Dodean RA, Li Y, Kelly JX. RSC Adv. 2019; 9: 42284
38 Fang Y, Rogness DC, Larock RC, Shi F. J. Org. Chem. 2012; 77: 6262
39 Li XA, Wang HL, Yang SD. Org. Lett. 2013; 15: 1794

Supplementary Material

Supporting Information