Four-component synthesis of polyhydroquinolines under catalyst- and solvent-free conventional heating conditions: mechanistic studies
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Author list: Mayurachayakul P., Pluempanupat W., Srisuwannaket C., Chantarasriwong O.
Publisher: Royal Society of Chemistry
Publication year: 2017
Journal: RSC Advances (2046-2069)
Volume number: 7
Issue number: 89
Start page: 56764
End page: 56770
Number of pages: 7
ISSN: 2046-2069
eISSN: 2046-2069
Languages: English-Great Britain (EN-GB)
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Abstract
A convenient and environmentally friendly procedure for the synthesis of polyhydroquinolines via a one-pot, four component condensation of different aromatic aldehydes with dimedone, ethyl acetoacetate and ammonium acetate has been developed. Upon heating at 100 ฐC, the desired products were produced in good to excellent yields with short reaction times under catalyst- and solvent-free conditions. Mechanistic studies indicated that two possible pathways can be accounted for the four-component synthesis of polyhydroquinolines. Unexpectedly, the first involves a nucleophilic attack of a Michael intermediate by an enamine, followed by a retro-aldol-type reaction and a six-electron ring cyclization. The second, which was previously proposed, involves a Michael addition of a Knoevenagel intermediate and an enamine. ฉ The Royal Society of Chemistry 2017.
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