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[reaction: see text] A novel 2-pyridone synthesis via nucleophilic addition of malonic esters to alkynyl imines has been developed. The reaction of dialkylalkyl sodiomalonates with alkynyl imines provided 2-pyridones in good to excellent yields.
In the present study, the stereodivergent synthesis of both cis- and trans-beta-lactams is presented using the following three reactions: iminocyclobutenone formation, chemoselective reduction of imino groups, and thermal rearrangement of aminocyclobutenones as crucial steps, in which the starting materials, iminocyclobutenones, were readily synthesized… (More)
In the presence of silica gel and water, a mixture of ketene silyl acetals and 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane underwent 1,4- and subsequently 1,2-addition with N-allylidene-1,1-diphenylethanamine to give delta-hydroxyesters in good yields, where the allylideneamine was successfully used as an acrolein equivalent.
N-Allylideneamines 1a, b were prepared from acrolein and diphenylethyl or trityl amine in the presence of Ti(OEt)4. Double nucleophilic addition of various ketene silyl (thio)acetals and trimethylsilyl cyanide to these imines proceeded efficiently to give, after workup with TFA, homoglutamic acid derivatives 3 and valerolactam 5.
Growing interests in nitrogen-containing molecules involving bioactive and functional materials have stimulated the recent development of synthetic methodologies where nucleophilic addition reactions to imino carbons are utilized in crucial steps. This article summarizes double nucleophilic addition reactions with alpha,beta-unsaturated aldimines, addition… (More)