Catalytic Benzannulation Reactions of Enynones for Accessing Heterocycle-Incorporating Diarylmethanes

Jia-Yin Wang; Guigen Li; Wen-Juan Hao; Bo Jiang

doi:10.1055/a-1971-6187

Synlett, Table of Contents

Synlett 2023; 34(03): 243-248
DOI: 10.1055/a-1971-6187

letter

Catalytic Benzannulation Reactions of Enynones for Accessing Heterocycle-Incorporating Diarylmethanes

Jia-Yin Wang

^aSchool of Pharmacy, Changzhou University, Changzhou 213164, P. R. of China

^bInstitute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

,

Guigen Li∗

^bInstitute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

^cDepartment of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, USA

,

Wen-Juan Hao

^dSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China

,

Bo Jiang∗

^dSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China

› Author Affiliations

Abstract

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Abstract

Two catalytic benzannulation/1,4-addition cascades of available enynones with indoles or tetronic acid-derived enamino lactones as C-nucleophiles are reported, producing 53 examples of heterocycle-incorporating diarylmethanes with moderate to excellent yields. The combination of AgOTf and Sc(OTf)₃ permits bimetallic synergistic catalysis of the reaction of enynones with indoles to access 35 triarylmethanes in generally good yields with ortho-naphthoquinone methides, generated in situ, as the key intermediates. Exchanging indoles for tetronic acid-derived enamino lactones resulted in 18 diarylmethanes by the Ag-catalyzed benzannulation/1,4-addition cascade. Both reactions are advantageous for their high atom utilization and mild reaction conditions, providing intriguing complementary approaches for the direct syntheses of new heterocycle-containing diarylmethanes.

Key words

triarylmethanes - diarylmethanes - benzannulation - 1,4-addition - cascade reaction - enamino lactones

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References

References and Notes

1a Duxbury DF. Chem. Rev. 1993; 93: 381
1b Nair V, Thomas S, Mathew SC, Abhilash KG. Tetrahedron 2006; 62: 6731
1c Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Chem. Rev. 2010; 110: 2250

2a Finocchiaro P, Gust D, Mislow K. J. Am. Chem. Soc. 1974; 96: 3198
2b Dothager RS, Putt KS, Allen BJ, Leslie BJ, Nesterenko V, Hergenrother PJ. J. Am. Chem. Soc. 2005; 127: 8686
2c Palchaudhuri R, Nesterenko V, Hergenrother PJ. J. Am. Chem. Soc. 2008; 130: 10274
2d Gemma S, Campiani G, Butini S, Kukreja G, Joshi BP, Persico M, Catalanotti B, Novellino E, Fattorusso E, Nacci V, Savini L, Taramelli D, Basilico N, Morace G, Yardley V, Fattorusso C. J. Med. Chem. 2007; 50: 595
2e Snyder SA, Breazzano SP, Ross AG, Lin Y, Zografos AL. J. Am. Chem. Soc. 2009; 131: 1753
2f Mibu N, Yokomizo K, Uyeda M, Sumoto K. Chem. Pharm. Bull. 2005; 53: 1171
2g Mibu N, Yokomizo K, Miyata T, Sumoto K. J. Heterocycl. Chem. 2010; 47: 1434
2h Panda G, Shagufta Shagufta, Mishra JK, Chaturvedi V, Srivastava AK, Srivastava R, Srivastava BS. Bioorg. Med. Chem. 2004; 12: 5269
2i Panda G, Shagufta Shagufta, Srivastava AK, Sinha S. Bioorg. Med. Chem. Lett. 2005; 15: 5222
2j Kashyap VK, Gupta RK, Shrivastava R, Srivastava BS, Srivastava R, Parai MK, Singh P, Bera S, Panda G. J. Antimicrob. Chemother. 2012; 67: 1188

3a Cho SD, Yoon K, Chintharlapalli S, Abdelrahim M, Lei P, Hamilton S, Khan S, Ramaiah SK, Safe S. Cancer Res. 2007; 67: 674
3b Wood PM, Woo LW. L, Labrosse J.-R, Trusselle MN, Abbate S, Longhi G, Castiglioni E, Lebon F, Purohit A, Reed MJ, Potter BV. L. J. Med. Chem. 2008; 51: 4226
3c Mondal S, Panda G. RSC Adv. 2014; 4: 28317
3d Mondal S, Roy D, Panda G. ChemCatChem 2018; 10: 1941

4a Duan H, Meng L, Bao D, Zhang H, Li Y, Lei A. Angew. Chem. Int. Ed. 2010; 49: 6387
4b Schäfer G, Bode JW. Angew. Chem. Int. Ed. 2011; 50: 10913
4c Gao J, Wang J.-Q, Song Q.-W, He L.-N. Green Chem. 2011; 13: 1182
4d Khodaei MM, Nazari E. Tetrahedron Lett. 2012; 53: 5131
4e Thirupathi P and Kim S. S.;. J. Org. Chem. 2009; 74: 7755
4f Tangdenpaisal K, Phakhodee W, Ruchirawat S, Ploypradith P. Tetrahedron 2013; 69: 933
4g Singh P, Dinda SK, Shagufta Shagufta, Panda G. RSC Adv. 2013; 3: 12100
4h Wilsdorf M, Leichnitz D, Reissig H.-U. Org. Lett. 2013; 15: 2494

5a Liégault B, Renaud J.-L, Bruneau C. Chem. Soc. Rev. 2008; 37: 290
5b Bej A, Srimani D, Sarkar A. Green Chem. 2012; 14: 661
5c Endo K, Ishioka T, Ohkubo T, Shibata T. J. Org. Chem. 2012; 77: 7223
5d Amatore M, Gosmini C. Chem. Commun. 2008; 5019
5e Schade MA, Metzger A, Hug S, Knochel P. Chem. Commun. 2008; 3046
5f Manolikakes G, Hernandez CM, Schade MA, Metzger A, Knochel P. J. Org. Chem. 2008; 73: 8422
5g Duplais C, Krasovskiy A, Wattenberg A, Lipshutz BH. Chem. Commun. 2010; 46: 562
5h Knochel P, Schade MA, Bernhardt S, Manolikakes G, Metzger A, Piller FM, Rohbogner CJ, Mosrin M. Beilstein J. Org. Chem. 2011; 7: 1261
5i Chan DC. M, Rosowsky A. J. Org. Chem. 2005; 70: 1364

6a Zhao D, You J, Hu C. Chem. Eur. J. 2011; 17: 5466
6b Ge S, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 12837

7a Yang B, Gao S. Chem. Soc. Rev. 2018; 47: 7926
7b Osipov DV, Osyanin VA, Klimochkin YN. Russ. Chem. Rev. 2017; 86: 625
7c Li W, Xu X, Zhang P, Li P. Chem. Asian J. 2018; 13: 2350
7d Caruana L, Fochi M, Bernardi L. Molecules 2015; 20: 11733
7e Parra A, Tortosa M. ChemCatChem 2015; 7: 1524
7f Wang J.-Y, Hao W.-J, Tu S.-J, Jiang B. Org. Chem. Front. 2020; 7: 1743

8a Sawama Y, Shishido Y, Yanase T, Kawamoto K, Goto R, Monguchi Y, Kita Y, Sajiki H. Angew. Chem. Int. Ed. 2013; 52: 1515
8b Zhou D, Yu X, Zhang J, Wang W, Xie H. Org. Lett. 2018; 20: 174
8c Lukashenko AV, Osyanin VA, Osipov DV, Klimochkin YN. J. Org. Chem. 2017; 82: 1517
8d Büyükkidan B, Ceylan M. J. Chem. Res. 2003; 749
8e Taheri A, Lai B, Yang J, Zhang J, Gu Y. Tetrahedron 2016; 72: 479

9 Wu F, Zhu S. Org. Lett. 2019; 21: 1488
10 Wu F, Zhang L, Zhu S. Org. Chem. Front. 2020; 7: 3387

11a Wang D, Wang S.-C, Hao W.-J, Tu S.-J, Jiang B. Chin. J. Chem. 2021; 39: 106
11b Wang D, Wang S.-C, Hao W.-J, Tu S.-J, Jiang B. Adv. Synth. Catal. 2020; 362: 3416

12a Ji C.-L, Pan Y, Geng F.-Z, Hao W.-J, Tu S.-J, Jiang B. Org. Chem. Front. 2019; 6: 474
12b Chen K, Liu S, Wang D, Hao W.-J, Zhou P, Tu S.-J, Jiang B. J. Org. Chem. 2017; 82: 11524
12c Liu S, Chen K, Lan X.-C, Hao W.-J, Li G, Tu S.-J, Jiang B. Chem. Commun. 2017; 53: 10692

13a Wu G, Liu Y, Yang Z, Katakam N, Rouh H, Ahmed S, Unruh D, Surowiec K, Li G. Research 2019; 6717104
13b Liu Y, Wu G, Yang Z, Rouh H, Katakam N, Ahmed S, Unruh D, Cui Z, Lischka H, Li G. Sci. China Chem. 2020; 63: 692-698
13c Wang J.-Y, Tang Y, Wu G.-Z, Zhang S, Rouh H, Jin S, Xu T, Wang Y, Unruh D, Surowiec K, Ma Y, Li Y, Katz C, Liang H, Cong W, Li G. Chem. Eur. J. 2022; 28: e202200183
13d Tang Y, Jin S, Zhang S, Wu G.-Z, Wang J.-Y, Xu T, Wang Y, Unruh D, Surowiec K, Ma Y, Wang S, Katz C, Liang H, Li Y, Cong W, Li G. Research 2022; 9847949
13e Rouh H, Tang Y, Xu T, Yuan Q, Zhang S, Wang J.-Y, Jin S, Wang Y, Pan J, Wood HL, McDonald JD, Li G. Research 2022; 9865108

14a 4-Methyl-2-[(1-methyl-1H-indol-3-yl)(phenyl)methyl]-1-naphthol (3a); Typical Procedure In a 10 mL reaction vial, enynone 1a (0.4 mmol, 98.4 mg), indole 2a (0.4 mmol, 52.4 mg), AgOTf (0.04 mmol, 10 mol%, 10.2 mg), and Sc(OTf)₃ (0.08 mmol, 20 mol%, 39.4 mg) were mixed in THF (4.0 mL). The mixture was stirred at rt under air for 5 h until the starting material was consumed [TLC, PE–EtOAc (10:1)]. Then the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, PE–EtOAc (30:1)] to give a white solid; yield: 129.7 mg (86%); mp 174–175 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.23–8.17 (m, 1 H), 7.95 (d, J = 7.6 Hz, 1 H), 7.57–7.48 (m, 2 H), 7.39–7.30 (m, 7 H), 7.28–7.24 (m, 1 H), 7.09–7.01 (m, 2 H), 6.60 (s, 1 H), 5.90 (s, 1 H), 5.70 (s, 1 H), 3.74 (s, 3 H), 2.59 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 148.1, 142.2, 137.8, 132.6, 129.0, 128.7, 128.7, 128.6, 127.3, 126.8, 126.1, 125.7, 125.5, 124.8, 124.0, 122.4, 122.3, 121.9, 119.9, 119.4, 115.6, 109.4, 45.0, 32.9, 18.9. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₇H₂₄NO: 378.1858; found: 378.1855.
14b 3-[(1-Hydroxy-4-methyl-2-naphthyl)(phenyl)methyl]-4-[(4-methylphenyl)amino]furan-2(5H)-one; Typical Procedure In a 10 mL reaction vial, enynone 1a (0.3 mmol, 73.8 mg), 4-(p-tolylamino)furan-2(5H)-one (4a, 0.3 mmol, 56.7 mg), and AgOTf (0.03 mmol, 10 mol%, 7.7 mg) were mixed in 1,4-dioxane (4.0 mL). The mixture was then stirred at 50 °C under air for 2 h until the starting material was consumed [TLC, PE–EtOAc (2:1)]. The solvent was then evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, PE–EtOAc (6:1)] to give a white solid; yield: 117.5 mg (90%); mp 159–161 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.38–8.22 (m, 1 H), 8.01–7.89 (m, 1 H), 7.58–7.51 (m, 2 H), 7.43–7.33 (m, 5 H), 7.12 (d, J = 8.8 Hz, 3 H), 6.87 (d, J = 6.4 Hz, 1 H), 6.79 (s, 1 H), 6.71 (d, J = 8.4 Hz, 2 H), 5.73 (s, 1 H), 4.89–4.79 (m, 2 H), 2.61 (s, 3 H), 2.32 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 176.4, 160.6, 147.9, 138.3, 135.7, 135.6, 132.7, 130.3, 129.1, 128.2, 127.6, 127.3, 127.2, 126.6, 126.1, 125.4, 124.0, 122.8, 121.8, 121.1, 98.3, 66.8, 40.5, 20.8, 19.0. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₉H₂₆NO₃: 436.1913; found: 436.1879.

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