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Synlett 2014; 25(14): 2054-2058
DOI: 10.1055/s-0033-1338656
DOI: 10.1055/s-0033-1338656
letter
MCPBA-Promoted Tandem Michael Addition–Intramolecular Cyclization of 2-Azido-β-amino Esters: Single Pot, Convenient Access to 1,2,4,5-Tetrasubstituted Imidazoles
Authors
Further Information
Publication History
Received: 07 May 2014
Accepted: 30 May 2014
Publication Date:
16 July 2014 (online)
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 - imidazolesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000083.
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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) Å3; 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 Kα (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.