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Synlett 2018; 29(16): 2199-2202
DOI: 10.1055/s-0037-1610234
DOI: 10.1055/s-0037-1610234
letter
Facile Construction of Hydantoin Scaffolds via a Post-Ugi Cascade Reaction
This work was supported by the Chongqing Research Program of Basic Research and Frontier Technology (cstc2015jcyjA1328 and cstc2015zdcy-ztzx0191) and the Scientific Research Foundation of Chongqing University of Arts and Sciences (Grant Nos. R2013XY01 and R2013XY02).Further Information
Publication History
Received: 10 July 2018
Accepted after revision: 18 July 2018
Publication Date:
06 September 2018 (online)
◊ These authors contributed equally to this work
Abstract
A small series of hydantoins was efficiently synthesized via a two-step Ugi/cyclization reaction sequence using alkyne group as a leaving group under basic conditions. This microwave-assisted one-pot cyclization strategy could be applicable to other multicomponent reactions (MCRs) for synthesizing bioactive and drug-like hydantoins.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610234.
- Supporting Information
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- 22 General Procedure for the Preparation of Hydantoin Compound 7A solution of aniline (1.0 mmol), propiolic acid (1.0 mmol), benzaldehyde (1.0 mmol), and isonitrile (1.0 mmol) were mixed in methanol with stirring overnight at room temperature. The reaction mixture was monitored by TLC. When no isonitrile was left, the solvent was removed under a gentle stream of nitrogen. Then, the residue was diluted with CH3CN (5.0 mL) and K2CO3 (1.0 mmol) was added. The reaction mixture was treated in microwave at 100 °C for 10 min. After the microwave vial was cooled to room temperature, the reaction mixture was diluted with EtOAc (25 mL) and washed with water and brine. Then the organic layer was dried with Na2SO4 and concentrated. The residue was purified by silica gel column chromatography using a gradient of EtOAc/hexane (15–30%) to afford the relative targeted product 7.Analytical Data for Compound 7aWhite solid, 75%. 1H NMR (400 MHz, CDCl3): δ = 4.71–4.83 (q, J = 14.4 Hz, 2 H), 5.46 (s, 1 H), 7.05–7.09 (t, J = 7.6 Hz, 1 H), 7.23–7.27 (m, 2 H), 7.27–7.35 (m, 8 H), 7.43–7.47 (t, J = 8.8 Hz, 4 H). 13C NMR (100 MHz, CDCl3): δ = 169.59, 160.24, 154.41, 136.47, 135.75, 134.35, 130.37, 129.11, 128.74, 128.07, 124.75, 120.20, 119.01, 114.73, 112.21, 64.26, 42.90. HRMS (ESI): m/z calcd for C22H18N2O2 + [M + H]+: 343.14465; found: 343.14431.