The syn-selective conjugate addition of amines to enoates derived from d-mannitol

Barcellos, Júlio C. F.; Vilela, Guilherme V.M. de A.; Borges, Beatriz; Miranda, Maria F.F.; Dias, Ayres G.; Costa, Paulo R.R.

doi:10.1016/j.tetasy.2016.06.017

Cited by 4 publications

(2 citation statements)

References 42 publications

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“…First, we attempted to obtain the amides from the direct reaction of the 4‐ Z ester with amine, but the Michael addition of the amine to the double bond of 4‐ Z was formed as the only product, thus forming amino esters. In a recent study, Barcellos et al . reported the synthesis of amino esters from the selective addition of amines to the 4‐ Z ester.…”

Section: Resultsmentioning

confidence: 99%

“…First, we attempted to obtain the amides from the direct reaction of the 4-Z ester with amine, but the Michael addition of the amine to the double bond of 4-Z was formed as the only product, thus forming amino esters. In a recent study, Barcellos et al 26 reported the synthesis of amino esters from the selective addition of amines to the 4-Z ester. The scope of this reaction was evaluated by the authors through the study of the conjugate addition of a series of primary and secondary amines in different reaction conditions.…”

Section: Synthesis Of Amidesmentioning

confidence: 99%

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Synthesis, insecticidal activity, and phytotoxicity of novel chiral amides

Aguiar

Alvarenga

Silva

et al. 2019

Pest Management Science

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BACKGROUND The lesser grain borer, Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae), is an important pest of stored grains worldwide. Chemical control is the main method used to manage this pest, but the continuous use of insecticides can lead to the selection of resistant R. dominica strains. Thus, there is a constant demand for the development of new insecticide molecules. This study describes the synthesis of 14 chiral amides and evaluation of their insecticidal activity against R. dominica. Their phytotoxicity to wheat (Triticum sativum) seeds is also evaluated. RESULTS In the screening assay, compounds 8i and 8j caused 100% and 87% mortality of R. dominica. These values did not differ from the mortality caused by Bifenthrin® (75%). Amide 8i presented similar toxicity (LD50 = 27.98 µmol g−1, CI95 = 25.14–30.71) and speed of action (LT50 = 22 h, CI95 = 19.34–24.66) to amide 8j (LD50 = 29.37 µmol g−1, CI95 = 27.43–31.09, and LT50 = 19 h, CI95 = 17.05–20.95) against the pest. Both amides inhibited less than 44% of wheat growth. CONCLUSION Among the tested amides, only 8i and 8j were effective in R. dominica control and presented no considerable phytotoxicity towards wheat seeds. Therefore, these amides are promising as insecticides for the management of R. dominica. © 2018 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Amidesmentioning

confidence: 99%