Solid-phase Synthesis of a Novel Kind of Hydroxylated Heterocyclic Ketene Aminals

An efficient solid-phase synthesis method for novel heterocyclic ketene aminals containing a hydroxyl group has been developed. The loading of the substrate on the resin through the hydroxyl group and the protection of the amine by the Schiff base were the key steps in the synthesis.

Synthesis of O-Glycosides of Heteroatom Aroyl-Substituted Heterocyclic Ketene Aminals

Heteroatom aroyl-substituted heterocyclic ketene aminals 1 reacted with 2,3,4,6-tetra-O-acetyl-α-glucopyranosyl bromide 2 under the catalysis of Hg(CN)2 or CaH2 to give E- or Z-O-glycosides of heterocyclic ketene aminals 3 or 4 in moderate yields.

O-Maltosylation of Heterocyclic Ketene Aminals

The stereoselective synthesis of O-maltosides by reacting benzoyl-substituted heterocyclic ketene aminals 1 or 2 with acetylated maltosyl bromide 3 was investigated. Compounds 1 or 2 reacted with 3 in the presence of mercuric cyanide to give O-maltosides 4 or 5 with E-configuration. While 1 reacted with 3 in the presence of calcium hydride to give O-maltosides 6 with Z-configuration.

A novel and facile synthesis of 2-oxo-1,2-dihydropyridine-fused 1,3-diazaheterocycles via heterocyclic ketene aminals and Konevenagel adducts formed by phthalic anhydride and ethyl cyanacetate

An efficient synthetic pathway to 2-oxo-1,2-dihydropyridine-fused 1,3-diaza heterocycles from heterocyclic ketene aminals,phathalic anhydride and ethyl cyanacetate was established.This protocol involved aza-ene reaction/imine-enamine tautomerization/enamine-ester exchange/ring-opening reaction sequence.

新型环状杂环烯酮缩胺的合成

杂环烯酮缩胺是一类用途广泛的合成子,常被用来合成一些用常规方法不易合成的稠杂环化合物.为了进一步研究杂环烯酮缩胺的结构对其反应性能的影响,以1,3-环己二酮为原料,经过碱化﹑加成﹑烷基化3步反应制备了烯酮缩二硫醚,再分别与乙二胺﹑丙二胺反应,得到了一类新型的环状杂环烯酮缩胺.

An environmentally benign multi-component reaction:Highly regioselective synthesis of functionalized 2-(diarylphosphoryl)-1,2-dihydro-pyridine derivatives

A novel protocol was developed for the construction of highly functionalized 2-(diarylphosphoryl)-1,2-dihydropyridine derivatives(DAPDHPs)from 3-formylchromones(1),heterocyclic ketene aminals(HKAs,2),and phosphine oxides(R_(2)P(O)H,3)via a novel,one-pot cascade reaction.Optimization of the reaction conditions determined that refluxing the mixture of the 3-formylchromones,HKAs,and various R_(2)P(O)H in propylene carbonate(PC)in the presence of triethylamine as a base facilitated the highest yields of the DAPDHP products.This cascade reaction,which involved the cleavage of one C-O bond in the 3-formylchromone substrates and the formation of three new bonds(one C-C,one C-N,and one C-P bond),enabled the synthesis of a small library of DAPDHP products.The dearomatized DAPDHP products were formed by the regioselective nucleophilic addition of the R_(2)P(O)H reagents to the intermediate pyridinium salts 8.This approach has several advantages such as the use of an environmentally-friendly solvent,simple and practical operation(with filtration and washing without column chromatography separation),good yields,and a product with potential biological activity.