Knoevenagel-Cyclization Cascade Reactions of Substituted 5,6-Dihydro-2H-Pyran Derivatives was written by Kiraly, Sandor Balazs;Benyei, Attila;Lisztes, Erika;Biro, Tamas;Toth, Balazs Istvan;Kurtan, Tibor. And the article was included in European Journal of Organic Chemistry in 2021.Recommanded Product: 5,6-Dihydro-2H-pyran-3-carbaldehyde This article mentions the following:
The diastereoselective domino-Knoevenagel-IMHDA reactions of 5,6-dihydro-2H-pyran derivatives containing an o-formylaryl amine or ether moiety were performed with active methylene reagents. In the spiro heterocyclic products such as I representing a novel skeleton, a tetrahydroquinoline or chroman unit was fused with two pyran rings and the bridgehead carbon atoms were chirality centers formed diastereoselectively. Depending on the substitution pattern, a domino Knoevenagel-[1,5]-hydride shift-cyclization sequence was identified as a competing pathway, which resulted in the formation of tetrahydroquinoline derivatives such as II with a 5,6-dihydro-2H-pyran-3-yl substituent. The relative configurations of the products were determined by means of the characteristic NOE correlations and single crystal X-ray diffraction anal. Antiproliferative activity assays of two products against A2780 and WM35 human cancer cell lines showed low micromolar IC50 values down to 2.99μM. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Recommanded Product: 5,6-Dihydro-2H-pyran-3-carbaldehyde).
5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.Recommanded Product: 5,6-Dihydro-2H-pyran-3-carbaldehyde
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics