Copper-Catalyzed Tandem Reactions of 2-Iodobenzamides with Sodium Azide: An Efficient Synthesis of [1,2,3]Triazolo[1,5-a][1,4]-benzodiazepin-6(5H)-ones

Abstract

Copper-catalyzed tandem reactions between 2-iodobenzamides with a propargyl group on the nitrogen atom moiety and sodium azide are presented, providing an efficient method for the synthesis of 3-substituted [1,2,3]triazolo[1,5-a][1,4]benzodiazepin-6(5H)-ones under mild conditions in moderate yields.

Key words

tandem reactions - copper-catalyzed - [1,2,3]triazolo[1,5-a][1,4]benzodiazepin-6(5H)-one - 2-iodobenzamides -

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• 14 3,5-Diphenyl-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]-diazepin-6(5H)-one (4a); Typical Procedure 2-Iodobenzamides 5 (0.3 mmol), NaN₃ (0.36 mmol), CuI (0.03 mmol), N,N′-dimethylethylenediamine (0.06 mmol), and DMSO (1 mL) and H₂O (0.2 mL) were added into a Schlenk tube at r.t. under N₂. The reaction mixture was stirred at 90 °C until the reaction was complete, as monitored by TLC. Then the reaction mixture was cooled, H₂O was added, the aqueous layer was extracted with CH₂Cl₂ (3 × 20 mL), and dried over MgSO₄. After filtration and removal of the solvent in vacuo, the residues were purified with flash chromatography (silica gel; PE–EtOAc, 4:1 v/v) to afford 4 as a yellow solid; mp 208–210 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.19 (d, J = 7.7 Hz, 1 H), 8.12 (d, J = 8.0 Hz, 1 H), 7.78 (t, J = 7.4 Hz, 1 H), 7.63 (t, J = 7.6 Hz, 1 H), 7.45–7.40 (m, 4 H), 7.36–7.34 (m, 4 H), 7.26 (d, J = 7.6 Hz, 2 H), 5.00 (s, 2 H). ¹³C NMR (125 MHz, CDCl₃): δ = 166.1, 143.6, 142.1, 133.2, 132.9, 132.6, 130.7, 129.7, 129.6, 129.3, 129.0, 128.7, 127.8, 127.4, 127.2, 126.3, 122.7, 43.8. IR: 1643, 1492, 1403, 753, 695 cm^–1. ESI-HRMS: m/z calcd for C₂₂H₁₇N₄O [M + H]⁺: 353.1397; found: 353.1412.