Cascade Reaction of 3-Phenacylideneoxindoles with Trimethylsilyl Cyanide: Synthesis of Furan-Fused 1,3-Benzodiazepin-2-one Derivatives

Abstract

A cascade reaction of 3-phenacylideneoxindoles with trimethylsilyl cyanide is described. This method provides an efficient route for the synthesis of furan-fused 1,3-benzodiazepin-2-one derivatives by simply refluxing a reaction mixture of various 3-phenacylideneoxindoles with trimethylsilyl cyanide in the presence of H₂O and K₂CO₃.

Key words

phenacylideneoxindoles - trimethylsilyl cyanide - cascade reaction - furobenzodiazepines

Publication History

Received: 09 October 2021

Accepted after revision: 08 January 2022

Article published online:
28 January 2022

• References and Notes

• 1a Magli E, Fattorusso C, Persico M, Corvino A, Esposito G, Fiorino F, Luciano P, Perissutti E, Santagada V, Severino B, Tedeschi V, Pannaccione A, Pignataro G, Caliendo G, Annunziato L, Secondo A, Frecentese F. J. Med. Chem. 2021; 64: 17901
• 1b Mantaj J, Jackson PM, Rahman KM, Thurston DE. Angew. Chem. Int. Ed. 2017; 56: 462
• 1c Arora N, Dhiman P, Kumar S, Singh G, Monga V. Bioorg. Chem. 2020; 97: 103668
• 1d Verma S, Kumar S. Mini-Rev. Org. Chem. 2017; 14: 453
• 2a Joshi P, Anderson C, Binch H, Hadida S, Yoo S, Bergeron D, Decker C, terHaar E, Moore J, Garcia-Guzman M, Termin A. Bioorg. Med. Chem. Lett. 2014; 24: 845
• 2b Sabnis RW. ACS Med. Chem. Lett. 2021; 12: 1530
• 2c Erickson GA, Hatcher MA, Journet M, Kowalski JA, Lovelace TC, Pink CJ, Xie S. J. Org. Chem. 2021; in press DOI: 10.1021/acs.joc.1c00563.
• 2d El-Subbagh HI, Hassan GS, El-Messery SM, Al-Rashood ST, Al-Omary FA, Abulfadl YS, Shabayek MI. Eur. J. Med. Chem. 2014; 74: 234
• 2e Mayer P, Brunel P, Chaplain C, Piedecoq C, Calmel F, Schambel P, Chopin P, Wurch T, Pauwels PJ, Marien M, Vidaluc J.-L, Imbert T. J. Med. Chem. 2000; 43: 3653
• 2f Corsi L, Geminiani E, Avallone R, Baraldi M. Life Sci. 2005; 76: 2523
• 2g Costa B, Salvetti A, Rossi L, Spinetti F, Lena A, Chelli B, Rechichi M, Pozzo ED, Gremigni V, Martini C. Mol. Pharmacol. 2006; 69: 37
• 2h Rodgers JD, Cocuzza AJ, Bilder DM. US 6204262, 2001

For syntheses of 1,4-benzodiazepines, see:
• 3a Velasco-Rubio Á, Bernárdez R, Varela JA, Saá C. J. Org. Chem. 2021; 86: 10889
• 3b Shin J, Lee J, Ko D, De N, Yoo EJ. Org. Lett. 2017; 19: 2901
• 3c Obara N, Watanabe T, Asakawa T, Kan T, Tanaka T. Synlett 2018; 29: 1639
• 3d Smits G, Zemribo R. Synlett 2015; 26: 2272
• 3e Van Den Hauwe R, Elsocht M, Hollanders C, Ballet S. Synlett 2021; 32: 1719
• 3f Malik N, Iyamu ID, Scheidt KA, Schiltz GE. Tetrahedron Lett. 2018; 59: 1513

For syntheses of 1,5-benzodiazepines, see:
• 3g Weers M, Luhning LH, Luhrs V, Brahms C, Doye S. Chem. Eur. J. 2017; 23: 1237
• 3h Castillo J.-C, Presset M, Abonia R, Coquerel Y, Rodriguez J. Eur. J. Org. Chem. 2012; 2338
• 3i Fu X, Feng J, Dong Z, Lin L, Liu X, Feng X. Eur. J. Org. Chem. 2011; 2011: 5233
• 3j Yang G.-f, Li G.-x, Huang J, Fu D.-q, Nie X.-k, Cui X, Zhao J.-z, Tang Z. J. Org. Chem. 2021; 86: 5110
• 3k Dai Z, Tian Q, Li Y, Shang S, Luo W, Wang X, Li D, Zhang Y, Li Z, Yuan J. Molecules 2019; 24: 4224
• 3l Sun Y.-W, Bei Y.-M, Wang L.-Z. Org. Biomol. Chem. 2019; 17: 930
• 3m Young J, Schäfer C, Solan A, Baldrica A, Belcher M, Nişanci B, Wheeler KA, Trivedi ER, Török B, Dembinski R. RSC Adv. 2016; 6: 107081
• 3n Dai-Il J, Tae-wonchoi C, Yun-Young K, In-Shik K, You-Mi P, Yong-Gyun L, Doo-Hee J. Synth. Commun. 1999; 29: 1941
• 3o Rueping M, Borrmann R, Koenigs R, Zoller J. Synthesis 2017; 49: 310
• 3p Obara N, Watanabe T, Asakawa T, Kan T, Tanaka T. Synthesis 2019; 51: 2198
• 3q Nardi M, Cozza A, Maiuolo L, Oliverio M, Procopio A. Tetrahedron Lett. 2011; 52: 4827

For syntheses of benzodiazepines, see:
• 3r Archer GA, Sternbach LH. Chem. Rev. 1968; 68: 747
• 3s Mahdavi M, Pedrood K, Montazer MN, Larijani B. Synthesis 2021; 53: 2342
• 4a Dengiz C, Özcan S, Şahin E, Balci M. Synthesis 2010; 1365
• 4b Smolobochkin AV, Gazizov AS, Otegen NK, Voronina JK, Strelnik AG, Samigullina AI, Burilov AR, Pudovik MA. Synthesis 2020; 52: 3263
• 4c Wang G, Liu C, Li B, Wang Y, Van Hecke K, Van der Eycken EV, Pereshivko OP, Peshkov VA. Tetrahedron 2017; 73: 6372
• 4d Yoshida T, Kambe N, Murai S, Sonoda N. Tetrahedron Lett. 1986; 27: 3037
• 4e Han X, Civiello RL, Mercer SE, Macor JE, Dubowchik GM. Tetrahedron Lett. 2009; 50: 386
• 5a Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
• 5b Shen K, Liu X, Lin L, Feng X. Chem. Sci. 2012; 3: 327
• 5c Dalpozzo R, Bartoli G, Bencivenni G. Chem. Soc. Rev. 2012; 41: 7247
• 5d Dhokne P, Sakla AP, Shankaraiah N. Eur. J. Med. Chem. 2021; 216: 113334
• 5e Saeed R, Sakla AP, Shankaraiah N. Org. Biomol. Chem. 2021; 19: 7768
• 5f Cao Z.-Y, Wang Y.-H, Zeng X.-P, Zhou J. Tetrahedron Lett. 2014; 55: 2571
• 6a Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
• 6b Sharma BM, Yadav M, Gonnade RG, Kumar P. Eur. J. Org. Chem. 2017; 2603
• 7 Lu Y.-L, Sun J, Xie Y.-J, Yan C.-G. RSC Adv. 2016; 6: 23390
• 8 CCDC 2110159 contains the supplementary crystallographic data for compound 2d. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
• 9a Dai L, Liu W, Zhou Y, Zeng Z, Hu X, Cao W, Feng X. Angew. Chem. Int. Ed. 2021; 60: 26599
• 9b Yu F, Yan S, Hu L, Wang Y, Lin J. Org. Lett. 2011; 13: 4782
• 9c Sun J, Sun Y, Gong H, Xie Y.-J, Yan C.-G. Org. Lett. 2012; 14: 5172
• 9d Jiang B, Wang X, Xu H.-W, Tu M.-S, Tu S.-J, Li G. Org. Lett. 2013; 15: 1540
• 9e Wang H, Li L, Lin W, Xu P, Huang Z, Shi D. Org. Lett. 2012; 14: 4598
• 10a Wang Y, Wei Z, Cao J, Liang D, Lin Y, Duan H. New J. Chem. 2021; 45: 2609
• 10b Chen W.-B, Wu Z.-J, Pei Q.-L, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2010; 12: 3132
• 11 Du Y, Li Z. Synth. Commun. 2019; 49: 65
• 12 5-Oxo-2-phenyl-5,6-dihydro-4H-furo[2,3-d][1,3]benzodiazepine-1-carbonitrile; Typical Procedure K₂CO₃ (69.1 mg, 0.5 mmol) and H₂O (45 mg, 2.5 mmol) were added sequentially to a solution of phenacylideneoxindole 1a (124.5 mg, 0.5 mmol) and TMSCN (124 mg, 1.25 mmol) in 1,4-dioxane (2 mL), and the mixture was stirred for 1 h at 100 ℃ (oil bath) until the reaction was complete (TLC; PE–EtOAc–MeOH, 10:3:1). An equal volume of H₂O was added to the reaction system, and the product was collected by filtration and washed with EtOAc to give a pale-yellow solid; yield: 100.9 mg (67%); mp 255–257 ℃. IR (KBr): 3268.73, 2974.33, 2221.75, 1696.17, 1395.62 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆, TMS): δ = 10.54 (s, 1 H), 9.05 (s, 1 H), 7.87 (d, J = 7.6 Hz, 2 H), 7.61 (t, J = 7.6 Hz, 2 H), 7.55 (t, J = 8.8 Hz, 2 H), 7.30 (t, J = 7.2 Hz, 1 H), 7.21 (t, J = 7.2 Hz, 1 H), 7.12 (d, J = 8.0 Hz, 1 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 160.94, 154.47, 145.82, 137.79, 130.64, 129.92, 129.40, 127.59, 125.73, 125.05, 124.89, 122.35, 120.50, 115.03, 104.84, 90.61. HRMS (ESI): m/z [M – H]^– calcd for C₁₈H₁₀N₃O₂: 300.0778; found: 300.0773.