A Facile Synthesis of 5-Acyl-6-alkyl/aryl-2,2-dimethyl-1,3-dioxin-4-ones

SmCl3-Catalyzed C-Acylation of 1,3-Dicarbonyl Compounds and Malononitrile

“…In most cases, 1,3,3‘-triketones are prepared by C -acylation of 1,3-dicarbonyl compounds. − Nevertheless, these methods usually require the use of stoichiometric amounts of strong bases such as EtONa, BaH 2 , EtMgBr, n -BuLi, or powerful reductive metals like Na, which are not suitable for sensitive substrates. Notably, Rathke and Cowan developed a MgCl 2 -promoted C -acylation of 1,3-dicarbonyl compounds . Although these possess many potential advantages, the main limitation of this strategy is that a stoichiometric amount of Lewis acid and 2 equiv of tertiary amine additive are required.…”

Metal- and Base-Free Combinatorial Reaction for C-Acylation of 1,3-Diketo Compounds in Vegetable Oil: The Effect of Natural Oil

“…1,3-Dioxin-4-one derivatives are potential precursors for important heterocyclic compounds and phenol derivatives. , Solanoeclepin A is an active natural hatching agent of the potatocyst nematode and is synthesized from 1,3-dioxin-4-one derivatives. Another example is (S)-(-)-zearalenone that is potent estrogen agonist and is also obtained from 1,3-dioxin-4-one derivatives.…”

Synthesis and Biological Properties of 4‐Substituted Quinolin‐2(1H)‐one Analogues.

“…In this condensation reaction, we found that the magnesium ethoxide was the most effective among bases such as sodium ethoxide, sodium hydride, sodium 3-aminoproylamide (NAPA), potassium 3-aminopropylamide (KAPA), and potassium t e rt-butoxide. It seems probable that the effectiveness of magnesium ethoxide can be explained in part by a magnesium chelation effect [15]. The keto diesters 2 c , d were smoothly transformed to 4-hydroxyquinolone compounds Treatment of diethyl 4,5-difluoro-2-nitrobenzoyl-malonate (2 c) and diethyl 4-chloro-2-nitrobenzoyl-malonate (2d) with p-toluenesulfonic acid gave ethyl 3,4-difluoro-2nitrobenzoylacetate (5 a) and ethyl 4-chloro-2-nitrobenzoylacetate (5 b), respectively, which were used without further purification for the next step.…”