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Novel synthesis of oxoacetamides via reaction of salicylaldehyde and isocyanide under mild reaction condition.

ABSTRACT: A convenient procedure for the formation of oxoacetamides derivatives is reported via the reaction of salicylaldehyde and alkyl isocyanide in a simple process without the use of any catalyst or metal promoters in DCM at room temperature. The structure of all obtained derivatives were determined by elemental and spectral analyses. In this reaction, 1,3-dioxine-4,4-dicarboxamide was obtained as minor product. This process offers considerable advantages such as the simplicity of reaction, regioselectivity, and the use of commercially available materials.

SUBMITTER: Bayat M

PROVIDER: S-EPMC7260292 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Novel synthesis of oxoacetamides <i>via</i> reaction of salicylaldehyde and isocyanide under mild reaction condition.

Bayat Mohammad M Nasri Shima S Alivisi Rahman R Jani Azadeh A

Heliyon 20200527 5

A convenient procedure for the formation of oxoacetamides derivatives is reported <i>via</i> the reaction of salicylaldehyde and alkyl isocyanide in a simple process without the use of any catalyst or metal promoters in DCM at room temperature. The structure of all obtained derivatives were determined by elemental and spectral analyses. In this reaction, 1,3-dioxine-4,4-dicarboxamide was obtained as minor product. This process offers considerable advantages such as the simplicity of reaction, re ...[more]

PMID: 32490258

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Project description:Background: Perivascular adipose tissue (PVAT), which surrounds most vessels, is de facto a distinct functional vascular layer actively contributing to vascular function and dysfunction. PVAT contributes to aortic remodeling by producing and releasing a large number of undetermined or less characterized factors that could target endothelial cells and vascular smooth muscle cells, and herein contribute to the maintenance of vessel homeostasis. Loss of PVAT in mice enhances atherosclerosis, but a causal relationship between PVAT and atherosclerosis and the possible underlying mechanisms remain to be addressed. The CDGSH iron sulfur domain 1 protein (referred to as mitoNEET), a mitochondrial outer membrane protein, regulates oxidative capacity and adipose tissue browning. The roles of mitoNEET in PVAT, especially in the development of atherosclerosis, are unknown. Methods: The brown adipocyte-specific mitoNEET transgenic mice were subjected to cold environmental stimulus. The metabolic rates and PVAT-dependent thermogenesis were investigated. Additionally, the brown adipocyte-specific mitoNEET transgenic mice were cross-bred with ApoE knockout mice. The ensuing mice were subsequently subjected to cold environmental stimulus and high cholesterol diet challenge for 3 months. The development of atherosclerosis was investigated. Results: Our data show that mitoNEET mRNA was downregulated in PVAT of both peroxisome proliferator-activated receptor gamma coactivator 1-alpha (Pgc1α)- and beta (Pgc1β)-knockout mice which are sensitive to cold. MitoNEET expression was higher in PVAT of wild type mice and increased upon cold stimulus. Transgenic mice with overexpression of mitoNEET in PVAT were cold resistant, and showed increased expression of thermogenic genes. ApoE knockout mice with mitoNEET overexpression in PVAT showed significant downregulation of inflammatory genes and showed reduced atherosclerosis development upon high fat diet feeding when kept in a 16°C environment. Conclusion: mitoNEET in PVAT is associated with PVAT-dependent thermogenesis and prevents atherosclerosis development. The results of this study provide new insights on PVAT and mitoNEET biology and atherosclerosis in cardiovascular diseases.

Project description:Ureido-functionalized compounds play an indispensable role in important biochemical processes, as well as chemical synthesis and production. Isocyanates, and KOCN in particular, are the preferred reagents for the ureido functionalization of amine-bearing compounds. In this study, we evaluate the potential of urea as a reagent to graft ureido groups onto amines at relatively low temperatures (<100 °C) in aqueous media. Urea is an inexpensive, non-toxic and biocompatible potential alternative to KOCN for ureido functionalization. From as early as 1864, urea was the go-to reagent for polyurea polycondensation, before falling into disuse after the advent of isocyanate chemistry. We systematically re-investigate the advantages and disadvantages of urea for amine transamidation. High ureido-functionalization conversion was obtained for a wide range of substrates, including primary and secondary amines and amino acids. Reaction times are nearly independent of substrate and pH, but excess urea is required for practically feasible reaction rates. Near full conversion of amines into ureido can be achieved within 10 h at 90 °C and within 24 h at 80 °C, and much slower reaction rates were determined at lower temperatures. The importance of the urea/amine ratio and the temperature dependence of the reaction rates indicate that urea decomposition into an isocyanic acid or a carbamate intermediate is the rate-limiting step. The presence of water leads to a modest increase in reaction rates, but the full conversion of amino groups into ureido groups is also possible in the absence of water in neat alcohol, consistent with a reaction mechanism mediated by an isocyanic acid intermediate (where the water assists in the proton transfer). Hence, the reaction with urea avoids the use of toxic isocyanate reagents by in situ generation of the reactive isocyanate intermediate, but the requirement to separate the excess urea from the reaction product remains a major disadvantage.

Dataset Information

Novel synthesis of oxoacetamides via reaction of salicylaldehyde and isocyanide under mild reaction condition.

Publications

Novel synthesis of oxoacetamides <i>via</i> reaction of salicylaldehyde and isocyanide under mild reaction condition.

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