Category: 119639-24-6

Waldner, Adrian published an article about the compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide( cas:119639-24-6,SMILESS:O=C(C=C1)N(C(C)(C)C)S1(=O)=O ).Formula: C7H11NO3S. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:119639-24-6) through the article.

The [4 + 2] cycloaddition of α,β-unsaturated hydrazones, Me2NN:CHCR:CHR1 (R = Me, Et, CHMe2, R1 = H; R = R1 = Me), (1-azabuta-1,3-dienes) with isothiazol-3(2H)-one 1,1-dioxide derivatives I (R2 = H, CMe3, Me3CCH2CMe2, 4-ClC6H4, PhCH2, 4-MeOC6H4CH2) affords, depending on the solvent used, picolinamides II or III, and 4-azasaccharin derivatives IV or V. The course of the reaction is mainly influenced by the substituent R2 of the dienophile I.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 119639-24-6, is researched, Molecular C7H11NO3S, about Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation, the main research direction is palladium catalyzed cycloaddition carbon hydrogen bond activation; amide lactam cycloaddition maleimide.Category: isothiazole.

Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) are required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3 + 2] reaction that utilizes C(sp3)-H activation to generate the three-carbon unit for formal cycloaddition with maleimides. We implemented a strategy where the initial C(sp3)-H activation/olefin insertion would trigger a relayed, second remote C(sp3)-H activation to complete a formal [3 + 2] cycloaddition The diastereoselectivity profile of this reaction resembles that of a typical pericyclic cycloaddition reaction in that the relationships between multiple stereocenters are exquisitely controlled in a single reaction. The key to success was the use of weakly coordinating amides as the directing group, as undesired Heck or alkylation pathways were preferred with other types of directing groups. The use of the pyridine-3-sulfonic acid ligands is critical to enable C(sp3)-H activation directed by this weak coordination. The method is compatible with a wide range of amide substrates, including lactams, which lead to novel spiro-bicyclic products. The [3 + 2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity. Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) is required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3 + 2] reaction that utilizes twofold C(sp3)-H activation to generate the three-carbon unit for formal cycloaddition The initial β-C(sp3)-H activation of aliphatic amide, followed by maleimide insertion, triggers a relayed, second C(sp3)-H activation to complete a formal [3 + 2] cycloaddition The key to success was the use of weakly coordinating amide as the directing group, as previous studies have shown that Heck or alkylation pathways are preferred when stronger-coordinating directing groups are used with maleimide coupling partners [e.g., N,N-dimethylpivalamide + N-(4-nitrophenyl)maleimide → I (87%, dr 6:1)]. To promote the amide-directed C(sp3)-H activation step, the use of pyridine-3-sulfonic acid ligands is crucial. This method is compatible with a wide range of amide substrates, including lactams, which lead to spiro-bicyclic products. The [3 + 2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of Medicinal Chemistry called Potent Benzimidazole Sulfonamide Protein Tyrosine Phosphatase 1B Inhibitors Containing the Heterocyclic (S)-Isothiazolidinone Phosphotyrosine Mimetic, Author is Combs, Andrew P.; Zhu, Wenyu; Crawley, Matthew L.; Glass, Brian; Polam, Padmaja; Sparks, Richard B.; Modi, Dilip; Takvorian, Amy; McLaughlin, Erin; Yue, Eddy W.; Wasserman, Zelda; Bower, Michael; Wei, Min; Rupar, Mark; Ala, Paul J.; Reid, Brian M.; Ellis, Dawn; Gonneville, Lucie; Emm, Thomas; Taylor, Nancy; Yeleswaram, Swamy; Li, Yanlong; Wynn, Richard; Burn, Timothy C.; Hollis, Gregory; Liu, Phillip C. C.; Metcalf, Brian, which mentions a compound: 119639-24-6, SMILESS is O=C(C=C1)N(C(C)(C)C)S1(=O)=O, Molecular C7H11NO3S, Recommanded Product: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide.

Potent nonpeptidic benzimidazole sulfonamide inhibitors of protein tyrosine phosphatase 1B (PTP1B) were derived from the optimization of a tripeptide containing the novel (S)-isothiazolidinone ((S)-IZD) phosphotyrosine (pTyr) mimetic. An x-ray cocrystal structure of inhibitor 46/PTP1B at 1.8 Å resolution demonstrated that the benzimidazole sulfonamides form a bidentate H bond to Asp-48 as designed, although the aryl group of the sulfonamide unexpectedly interacts intramolecularly in a pi-stacking manner with the benzimidazole. The ortho substitution to the (S)-IZD on the aryl ring afforded low nanomolar enzyme inhibitors of PTP1B that also displayed low caco-2 permeability and cellular activity in an insulin receptor (IR) phosphorylation assay and an Akt phosphorylation assay. The design, synthesis, and SAR of this novel series of benzimidazole sulfonamide containing (S)-IZD inhibitors of PTP1B are presented herein.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called A facile construction of 4-hydroxymethylbenzisothiazolone-1,1-dioxide, published in 1998-03-19, which mentions a compound: 119639-24-6, mainly applied to furylmethanol isothiazolone dioxide regioselective Diels Alder; hydroxymethylbenzisothiazolone regioselective preparation; benzisothiazolone hydroxymethyl regioselective preparation; MO Diels Alder furylmethanol isothiazolone dioxide; hydrogen bond furylmethanol isothiazolone dioxide cycloaddition, Related Products of 119639-24-6.

4-Hydroxymethylbenzisothiazolone-1,1-dioxide could be facilely synthesized via a highly regioselective Diels-Alder cycloaddition between furfuryl alc. and 2-(tert-butyl)-isothiazolone-1,1-dioxide, followed by aromatization of the adduct under basic conditions. A secondary effect from intramol. hydrogen bonding influences the regioselectivity of the cycloaddition Unequivocal proof of the regiochem. of the Diels-Alder reaction is provided by X-ray crystallog. and ab initio calculations showed electronic and steric effects on transition structure asynchronicity.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Formula: C7H11NO3S. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Synthesis of new biologically active isothiazolo[4,5-b]carbazole-type tetracyclic derivatives via an indole-2,3-quinodimethane approach. Author is Miambo, Raimundo F.; Laronze-Cochard, Marie; Lawson, Ata-Martin; Guillot, Regis; Baldeyrou, Brigitte; Lansiaux, Amelie; Supuran, Claudiu T.; Sapi, Janos.

A number of isothiazolo[4,5-b]carbazole derivatives were prepared via a Diels-Alder approach involving thermally induced indole-2,3-quinodimethane intermediates. Preliminary biol. tests revealed a GSK-3β kinase inhibitor (I) and some free NH group containing compounds (I, II, III) displayed selective human carbonic anhydrase I inhibitory activities.

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Isothiazole – Wikipedia,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Tilcotil studies. Part 2. [4 + 2] Additions with isothiazol-3(2H)-one 1,1-dioxide, the main research direction is bromosiothiazole dioxide Diels Alder siloxybutadiene; oxazole isothiazolone dioxide Diels Alder; saccharin sweetening agent; pyridoisothiazole; oxicam; tilcotil; piroxicam derivative.COA of Formula: C7H11NO3S.

The isothiazoles I (R = CMe3, CH2CO2Et, R1 = Br) are not only dipolarophiles but also reactive and versatile dienophiles, especially with oxy-substituted 1,3-butadienes, I readily combine in Diels-Alder fashion; the regiospecificity of the addition is governed by the carbonyl group of the dienophile, whereas the SO2 group can be ignored for the purpose of predicting regioselectivity. Upon dehydrobromination of the [4 + 2] adducts with DBN, the cycloaromatization process is completed, generating saccharin-like compounds Besides the parent saccharin, several hydroxylated derivatives, e.g., II (R2 = OH, R3 = H; R2 = R3 = OH) have been synthesized by this new method. II are of potential interest as non-nutritive sweetening agents. In an alternative version of this principle, the isothiazole I (R = CMe3, CH2CO2Et, CH2C6H4OMe-4, R1 = H) is reacted with the oxazole III, affording, after acid-promoted rearrangement, pyrido-annulated isothiazoles IV. Since both processes generate saccharin-related structures, they may serve in syntheses of oxicams and analogs of ipsapirone. To demonstrate the viability of the approach one representative of each series, has been converted to an oxicam.

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Isothiazole – Wikipedia,
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Category: isothiazole. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors. Author is Sparks, Richard B.; Polam, Padmaja; Zhu, Wenyu; Crawley, Matthew L.; Takvorian, Amy; McLaughlin, Erin; Wei, Min; Ala, Paul J.; Gonneville, Lucie; Taylor, Nancy; Li, Yanlong; Wynn, Richard; Burn, Timothy C.; Liu, Phillip C. C.; Combs, Andrew P..

Benzothiazole benzimidazole (S)-isothiazolidinone ((S)-IZD) derivatives 5 were discovered through a peptidomimetic modification of the tripeptide (S)-IZD protein tyrosine phosphatase 1B (PTP1B) inhibitor 1. These derivatives are potent, competitive, and reversible inhibitors of PTP1B with improved caco-2 permeability. An X-ray co-crystal structure of inhibitor 5/PTP1B at 2.2 Å resolution demonstrated that the benzothiazole benzimidazole forms bi-dentate H-bonds to Asp48, and the benzothiazole interacts with the surface of the protein in a solvent exposed region towards the C-site. The design, synthesis, and SAR of this novel series of benzothiazole benzimidazole containing (S)-IZD inhibitors of PTP1B are presented herein.

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Quality Control of 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about A facile construction of 4-hydroxymethylbenzisothiazolone-1,1-dioxide.

4-Hydroxymethylbenzisothiazolone-1,1-dioxide could be facilely synthesized via a highly regioselective Diels-Alder cycloaddition between furfuryl alc. and 2-(tert-butyl)-isothiazolone-1,1-dioxide, followed by aromatization of the adduct under basic conditions. A secondary effect from intramol. hydrogen bonding influences the regioselectivity of the cycloaddition Unequivocal proof of the regiochem. of the Diels-Alder reaction is provided by X-ray crystallog. and ab initio calculations showed electronic and steric effects on transition structure asynchronicity.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors, published in 2007-02-01, which mentions a compound: 119639-24-6, Name is 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, Molecular C7H11NO3S, Formula: C7H11NO3S.

Benzothiazole benzimidazole (S)-isothiazolidinone ((S)-IZD) derivatives 5 were discovered through a peptidomimetic modification of the tripeptide (S)-IZD protein tyrosine phosphatase 1B (PTP1B) inhibitor 1. These derivatives are potent, competitive, and reversible inhibitors of PTP1B with improved caco-2 permeability. An X-ray co-crystal structure of inhibitor 5/PTP1B at 2.2 Å resolution demonstrated that the benzothiazole benzimidazole forms bi-dentate H-bonds to Asp48, and the benzothiazole interacts with the surface of the protein in a solvent exposed region towards the C-site. The design, synthesis, and SAR of this novel series of benzothiazole benzimidazole containing (S)-IZD inhibitors of PTP1B are presented herein.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Beaudegnies, Renaud; Ghosez, Leon researched the compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide( cas:119639-24-6 ).Formula: C7H11NO3S.They published the article 《Asymmetric Diels-Alder reactions with chiral 1-azadienes》 about this compound( cas:119639-24-6 ) in Tetrahedron: Asymmetry. Keywords: asym Diels Alder azadiene; piperidine enantiomerically pure. We’ll tell you more about this compound (cas:119639-24-6).

Chiral 1-azadienes I (R1, R2 = H, Me) derived from α,β-unsaturated aldehyde and Enders’ hydrazines cycloadd to cyclic dienophiles with high facial selectivities. The adducts can be readily converted into enantiomerically pure piperidine derivatives, e.g. II.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com