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Convenient Novel Method to Access N-Benzylated Isatoic Anhydride: Reaction Behavior of Isatoic Anhydride with 4-Chlorobenzyl Chloride in the Presence of Bases.

ABSTRACT: Sodium hydride, potassium carbonate, and other bases are commonly used for N-alkylation of heterocyclic compounds. This report reveals the problems associated with N-benzylation of isatoic anhydride and identifies the plausible byproduct structures formed during the reaction. Subsequently, a novel breakthrough methodology has been developed using diisopropylamine and tetra butyl ammonium bromide. It gives excellent yields >88% in a short reaction time (2 h) at 30 °C with no byproducts, saving on processes as the pure product is directly obtained.

SUBMITTER: Verma E

PROVIDER: S-EPMC8015103 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide.

Project description:Synthetic methods used to generate substituted anilines and quinazolines, both privileged pharmacological structures, are cumbersome, hazardous or, in some cases, unavailable. We developed a straightforward method for making isatoic anhydride-8-amide from isatin-7-carboxylic acid as a tool to easily produce a range of quinazoline and substituted aniline derivatives using adaptable pH-sensitive cyclization chemistry. The approaches are inexpensive, simple, fast, efficient at room temperature and scalable, enabling the synthesis of both established and new quinazolines and also highly substituted anilines including cyano derivatives.

| S-EPMC6776664 | biostudies-literature

Photochemical Generation of Benzoazetinone by UV Excitation of Matrix-Isolated Precursors: Isatin or Isatoic Anhydride.

Project description:Benzoazetinone was photochemically generated by UV irradiation of isatin isolated in low-temperature Ar matrixes. Upon UV (λ = 278 nm) excitation of isatin, monomers of the compound underwent decarbonylation and the remaining part of the molecule adopted the benzoazetinone structure or the structure of its open-ring isomer α-iminoketene. The same products (benzoazetinone and α-iminoketene) were generated by UV (λ = 278 nm) induced decarboxylation of matrix-isolated monomers of isatoic anhydride. Photoproduced α-iminoketene appeared in the low-temperature matrixes as a mixture of syn and anti isomers. Photoproducts generated upon λ = 278 nm irradiation of matrix-isolated isatin were subsequently exposed to λ = 532 nm light. That irradiation resulted in the shift of the α-iminoketene-benzoazetinone population ratio in favor of the latter closed-ring structure. The next irradiation at 305 nm caused the shift of the α-iminoketene-benzoazetinone population ratio in the opposite direction, that is, in favor of the open-ring isomer. Neither benzoazetinone nor its α-iminoketene open-ring isomer was generated upon UV (λ = 278 nm) irradiation of phthalimide isolated in Ar matrixes. Instead, the UV-excited monomers of this compound underwent such phototransformations as oxo → hydroxy phototautomerism or degradation of the five-membered ring with release of HNCO and CO. The efficiency of these photoconversions was low.

| S-EPMC7590977 | biostudies-literature

Acid-Catalyzed Synthesis of Isatoic Anhydride-8-Secondary Amides Enables IASA Transformations for Medicinal Chemistry.

Project description:Quinazolin-dione-N-3-alklyl derivatives are the core scaffolds for several categories of bioactive small molecules, but current synthetic methods are costly, involve environmental hazards, and are not uniformly scalable. Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione-N-3-alkyls (isomers of isatoic-8-secondary amides (IASAs)) from isatin that take advantage of in situ capture of imidic acid under acidic conditions. We further show that this method can be used for the synthesis of a wide variety of derivatives with medicinal uses.

| S-EPMC9107799 | biostudies-literature

A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids.

Project description:We show a convenient decarboxylative aldol process using a scandium catalyst and a PYBOX ligand to generate a series of highly functionalized chiral α-hydroxy esters. The protocol tolerates a broad range of β-keto acids with inactivated aromatic and aliphatic α-keto esters. The possible mechanism is rationalized.

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Liver toxicity of dichloroacetyl chloride and dichloroacetic anhydride in female MRL +/+ mice

Project description:Dichloroacetyl chloride (DCAC) is a metabolic intermediate of trichloroethene (TCE), an industrial chemical and ubiquitous environmental contaminant. TCE and its metabolites have been implicated in the induction of organ-specific and systemic autoimmunity, in the acceleration of autoimmune responses, and in the development of liver toxicity. In humans, effects of environmental toxicants are often multifactorial and detected only after long-term exposure. Therefore, we developed a small-animal model to determine mechanisms by which DCAC and related acylating agents affect liver disease. Autoimmune-prone female MRL +/+ mice were injected i.p. with 0.2 mmole/kg of DCAC or the acylating agent dichloroacetic anhydride (DCAA) in corn oil twice weekly for six weeks. We then determined changes in the liver transcriptome using microarray gene expression analysis. After exposure to DCAC or DCAA, we observed changes in liver gene expression consistent with inflammatory processes. Both toxicants up-regulated expression of acute phase response and inflammatory genes. Further, metallothionein genes were strongly up-regulated, indicating effects of the toxicants on zinc ion homeostasis and stress responses. In addition, DCAC and DCAA induced up-regulation of several genes indicative of tumorogenesis. Microarray gene expression analysis using a restricted set of genes could be a valuable tool to screen for early changes in liver function following suspected exposure to environmental toxicants. Keywords: Response to acylating agents; inflammatory response; disease state analysis.

2008-01-31 | GSE5241 | GEO

Limonene-Based Epoxy: Anhydride Thermoset Reaction Study.

Project description:The development of epoxy thermosets from renewable resources is of paramount importance in a sustainable development context. In this paper, a novel bio-based epoxy monomer derived from limonene was synthesized without epichlorohydrine and characterized. In fact, this paper depicts the synthesis of bis-limonene oxide (bis-LO). However, intern epoxy rings generally exhibit a poor reactivity and allow reaction with anhydride. Therefore, we used a reaction model with hexahydro-4-methylphthalic anhydride to compare reactivity of terminal and interepoxy functions. We also studied the influence of methyl group on intern epoxy functions. Furthermore, the influence of epoxy:anhydride stoichiometry and initiator amount was studied. These studies allow to propose an optimized formulation of bis-LO. Finally, a bis-LO-based thermoset was obtained and characterized.

| S-EPMC6278336 | biostudies-literature

Convenient access to bicyclic and tricyclic diazenes.

Project description:Heating the tosylhydrazone of an omega-alkenyl ketone or aldehyde to reflux in toluene in the presence of K(2)CO(3) delivered the bicyclic diazene. Irradiation of the diazene converted it to the cyclopropane. This appears to be a generally useful method for the construction of substituted cyclopentanes and cyclohexanes.

| S-EPMC2765546 | biostudies-literature

Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives.

Project description:A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation-build-up strategy of the ethyl ester at the 3-position allowed for the construction of the ?-hydroxyacetic acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project.

| S-EPMC6178280 | biostudies-literature

Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: a rapid, convenient synthesis of isocyanates.

Project description:A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, -60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation.

| S-EPMC3102642 | biostudies-literature

Reaction of myoglobin with 3,3-tetramethyleneglutaric anhydride.

Project description:1. The extent of reaction of the protein with 3,3-tetramethyleneglutaric anhydride was measured by determining the loss of lysine and the equivalent appearance of 3,3-tetramethyleneglutarimidolysine in the hydrolysate at various time-intervals. Of the 19 lysine residues in sperm-whale myoglobin, three did not react with 3,3-tetramethyleneglutaric anhydride. Also, the N-terminal valine did not react. 2. Slight spectral changes were observed on modification of myoglobin. 3. Electrophoretic changes were great since the derivative was negative throughout the range pH6-8.8. 4. The derivative did not react with antisera to native sperm-whale myoglobin.

| S-EPMC1270270 | biostudies-other

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