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Catalytic methylation of aromatic amines with formic acid as the unique carbon and hydrogen source

A novel methodology is presented for the direct methylation of amines, using formic acid as a unique source of carbon and hydrogen. Based on ruthenium(II) catalysts, the formation of the N – CH3group proceeds via an efficient formylation/transfer hydrogenation pathway.

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Efficient synthesis of N-sulfonylacetamidines from propiolic acid by copper-catalyzed three-component coupling reactions

Using propiolic acid as one of the reacting components, a copper-catalyzed three-component reaction of sulfonyl azide and amines affords N-sulfonylacetamidines via a decarboxylation process in high yields under mild conditions. This one-pot method is efficient, general, and versatile. Georg Thieme Verlag Stuttgart New York.

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent

A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to Azixa (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Substitution at Tricoordinate Sulfur(IV). Rearrangement of Sulfinanilides to Anilino Sulfoxides

Seven N-methyl-N-aryl-p-toluenesulfinamides (1, 3-Me2NC6H4; 2, 3-MeOC6H4; 3, 4-MeOC6H4; 4, 3-MeC6H4; 5, Ph; 6, 3-ClC6H4; 7, 3-FC6H4), N-(3-methoxyphenyl)-p-toluenesulfinamide (8), and two N-methyl-N-aryl-methanesulfinamides (9, 3-Me2NC6H4; 10, 3-MeOC6H4) were prepared from the corresponding sulfinyl chloride and the substituted aniline.Sulfinanilides 2 and 7 were treated with alkyllithiums in vain attempts to induce rearrangement to the diaryl sulfoxides via endocyclic nucleophilic attack by carbon 2 of the aniline ring on sulfur.Instead, the alkyllithium cleaved the S-N bond to yield the aniline and alkyl p-tolyl sulfoxide.Upon treatment with gaseous HCl in chloroform, the sulfinanilides rearranged as follows: 1 gave 4-(dimethylamino)-2-(methylamino)-4′-methyldiphenyl sulfoxide (92percent yield), 2 gave 2-methoxy-4-(methylamino)-4′-methyldiphenyl sulfoxide (26percent yield) and 4-methoxy-2-(methylamino)-4′-methyldiphenyl sulfoxide (70percent yield), 4 gave 2-methyl-4-(methylamino)-4′-methyldiphenyl sulfoxide (71percent yield), 9 gave methyl 4-(dimethylamino)-2-(methylamino)phenylsulfoxide (20percent yield), and 10 gave methyl 2-methoxy-4-(methylamino)phenyl sulfoxide (5percent yield).Sulfinanilides 3 and 5-8 did not rearrange.A tentative mechanism for the rearrangement is proposed.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Palladium(II) Acetate-Catalyzed Dual C?H Functionalization and C?C Bond Formation: A Domino Reaction for the Synthesis of Functionalized (E)-Bisindole-2-ones from Diarylbut-2-ynediamides

A domino reaction of palladium(II)-catalyzed dual C?H functionalization with subsequent intramolecular annulation is presented. This method provides a convenient synthesis of a range of symmetrical and unsymmetrical biologically important (E)-bisindole-2-ones under extremely mild reaction conditions ? room temperature, green oxidant and no additive. The reaction mechanism is elucidated in light of the yield values as well as additional control experiment results. (Figure presented.).

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Synthesis of mono-N-substituted functionalized anilines

The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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3-Alkylperoxy-3-cyano-oxindoles from 2-Cyano-2-diazo-N-phenyl-acetamides via Cyclizing Carbene Insertion and Subsequent Radical Oxidation

A transition-metal-free one-pot sequence for the synthesis of 3-peroxy-substituted oxindoles from readily prepared 2-cyano-2-diazo-acetamides is reported. The two-step tandem process includes a highly efficient thermal intramolecular C-H-carbene insertion followed by a tetrabutylammonium iodide (TBAI) catalyzed radical C3-peroxy-functionalization. The protocol provides easy access to a new class of 3-cyano-3-peroxy-disubstituted oxindoles. Useful transformations to amides and alcohols are demonstrated.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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THERAPEUTIC COMPOUNDS FOR THE TREATMENT OF VIRAL INFECTIONS

Compounds of formula I or salts thereof are disclosed. Also disclosed are pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Microwave-assisted synthesis of pyrazolo[3,4-d]pyrimidines from 2-amino-4,6-dichloropyrimidine-5-carbaldehyde under solvent-free conditions

The microwave-induced synthesis of pyrazolo[3,4-d]pyrimidines 4 in the reaction of N4-substituted-2,4-diamino-6-chloro-5-carbaldehydes 3 with hydrazine is described here. Precursors 3 have been prepared by the mono-amination of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde 2 with aliphatic and aromatic amines. The reaction times with primary amines were relatively shorter than for secondary amines.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Transition-Metal-Free Thioamination of Arynes Using Sulfenamides

The insertion of arynes into the S-N sigma-bond of sulfenamides allowing the synthesis of o-sulfanylaniline derivatives with reasonable functional group compatibility is presented. The aryne generated from 2-(trimethylsilyl)aryl triflates using CsF in DME was the key for the success of this transition-metal-free thioamination reaction, which involves new C-N and C-S bond formations in a single step under mild conditions. Moreover, the synthetic potential of this method was demonstrated by the synthesis of the antidepressant drug vortioxetine.

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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem