MCPBA-Promoted Tandem Michael Addition–Intramolecular Cyclization of 2-Azido-β-amino Esters: Single Pot, Convenient Access to 1,2,4,5-Tetrasubstituted Imidazoles

Abstract

A simple, single-pot synthesis of tetrasubstituted imidazoles has been developed through the use of MCPBA-promoted tandem Michael addition–intramolecular cyclization of 2-azido-β-amino esters.

Key words

multicomponent reactions - small ring systems - Michael addition - intramolecular cyclization - imidazoles

• References and Notes

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• 37 Synthesis of 1-Aryl/Alkyl-2,5-distyryl-1H-imidazole-4-carboxylic Acid Methyl Ester 4; General Procedure: To a stirred solution of β-amino esters 2 and 3 (1 mmol) in anhydrous chloroform, MCPBA (1.5 mmol) was added and the reaction mixture was heated to reflux for 10–12 h. The progress of the reaction was monitored by TLC analysis. Upon completion, the reaction was quenched with water (20 mL) and extracted with chloroform (2 × 50 mL). The combined organic layers were dried over anhydrous Na₂SO₄, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate–hexane, 15:85) to afford 4 in good to excellent yield. 2,5-Distyryl-1-p-tolyl-1H-imidazole-4-carboxylic Acid Methyl Ester (4a): Pale-yellow solid; m.p. 122-123 °C; IR (KBr): 1617 cm^–1; ¹H NMR (300 MHz, CDCl₃): δ = 2.52 (s, 3 H, CH₃), 4.00 (s, 3 H, OCH₃), 6.47 (d, J = 16.2 Hz, 2 H, olefinic-H), 7.24–7.41 (m, 14 H, ArH), 7.52 (d, J = 16.5 Hz, 1 H, olefinic-H), 7.74 (d, J = 15.9 Hz, 1 H, olefinic-H); ¹³C NMR (125 MHz, CDCl₃): δ = 21.4, 52.0, 113.0, 114.6, 126.6, 127.0, 128.0, 128.2, 128.5, 128.6, 128.7, 130.2, 130.7, 133.3, 133.4, 135.1, 136.1, 136.7, 136.9, 140.2, 147.2, 164.1; HRMS (ESI-micrOTOF-QII): m/z [M + H]⁺ calcd for C₂₈H₂₄N₂O₂: 421.1838; found: 421.1847. Anal. Calcd (%) for C₂₈H₂₄N₂O₂: C, 79.98; H, 5.75; N, 6.66. Found: C, 80.12, H, 5.68, N, 6.77. X-ray Crystal Data and Structure Refinement for 4a: C₂₈H₂₄N₂O₂; monoclinic; space group P 21/c; a = 11.293 (4) Å, b = 7.318 (2) Å, c = 26.722 (9) Å, α = 90°, β = 95.244 (14)°, γ = 90°; V = 2199.1 (12) ų; Z = 4; D calcd. = 1.270 g/cm³; μ = 0.080 mm^–1, T = 100 (2) K; 2θ max = 27.61°, completeness to 2θ max = 99.4%, total reflections = 19830, independent (Rint = 0.1590), 5080 observed [I>2σ(I)]. Final R1 [I>2σ(I)] = 0.0732, wR2 (all data) = 0.1752, largest difference peak and hole 0.313 and –3.15 e.Å^–3. X-ray intensity data were obtained with a Bruker Apex-II CCD diffractometer using Mo K_α (λ = 0.71069 Å). The data were processed by SAINT. Lorentz and polarization effects and empirical corrections were applied by using SADABS from Bruker. CCDC-998758 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.