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

Publikationsverlauf

Eingereicht: 09. Oktober 2021

Angenommen nach Revision: 08. Januar 2022

Artikel online veröffentlicht:
28. Januar 2022

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• 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.