ChemInform Abstract: An Efficient Process for the Synthesis of trans-2,3-Disubstituted-2,3-dihydro-4H-1-benzopyran-4-ones (Chroman-4-ones)

Autor:	Eugene J. Vater, Xun Li, Richard W. Draper, Radha V. Iyer, Mohammad Ataur Rahman, Yuelie Lu, Bin Hu
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Yield (chemistry) Aryl Knoevenagel condensation Isopropyl alcohol General Medicine Piperidine Medicinal chemistry Catalysis Benzopyran
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
Popis:	The piperidine catalyzed Knoevenagel condensation of 2′-aryl/alkyl-2-hydroxyacetophenones 7 and aryl/alkylaldehydes 8 in refluxing isopropyl alcohol with azeotropic removal of water affords, in high yield, equilibrium mixtures of E - and Z -chalcones 9 and cis - and trans -chroman-4-ones 10 which are effectively isomerized in situ to the trans -2,3-diaryl/alkylchroman-4-ones, following the addition of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) to the cooled reaction mixture and may be isolated in high purities (91–99%) by simple filtration, with good to excellent yields (70–95%).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::808a89c3b4c9223c2ec566fc559792d4 https://doi.org/10.1002/chin.200026132 Zobrazit plný text záznamu Plný text