Tag: M.W:100-200

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1268340-93-7, is researched, SMILESS is F[B-](F)(C[NH+]1CCCCC1)F, Molecular C6H13BF3NJournal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Journal of Organic Chemistry called Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki-Miyaura Cross-Coupling Reactions, Author is Raushel, Jessica; Sandrock, Deidre L.; Josyula, Kanth V.; Pakyz, Deborah; Molander, Gary A., the main research direction is aminomethyltrifluoroborate potassium salt preparation Suzuki Miyaura cross coupling.Application In Synthesis of (Piperidinium-1-ylmethyl)trifluoroborate.

A reinvestigation into the chem. composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

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 [4+2] Cycloaddition of α,β-unsaturated hydrazones. 3. Isothiazolo[4,5-b]pyridin-3(2H)-one 1,1-dioxides (4-azasaccharin derivatives), the main research direction is unsaturated hydrazone cycloaddition isothiazolone dioxide; azabutadiene cycloaddition isothiazolone; solvent effect cycloaddition isothiazolone dioxide azabutadiene; isothiazolopyridinone dioxide; azasaccharin derivative.Safety of 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide.

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

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 Synthesis and Plant Growth Stimulating Action of 2-Amino-6-methylpyrimidine-4(3H)-thione Derivatives, published in 2020-03-31, which mentions a compound: 6307-44-4, Name is 2-Amino-6-methylpyrimidine-4-thiol, Molecular C5H7N3S, Name: 2-Amino-6-methylpyrimidine-4-thiol.

A series of new pyrimidine derivatives, e.g., I including those containing an azole or azine heterocycle linked through a sulfur atom or a thiomethylene group, was synthesized based on 2-amino-6-methylpyrimidine-4(3H)-thione. The synthesized compounds exhibited a pronounced stimulating effect on plants growth in the range of 43-96% compared to heteroauxin.

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Reference:
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.Erkin, A. V.; Gurzhiy, V. V.; Krutikov, V. I.; Neporozhneva, O. V. researched the compound: 2-Amino-6-methylpyrimidine-4-thiol( cas:6307-44-4 ).Formula: C5H7N3S.They published the article 《Quantum Chemistry, NMR Spectroscopy, and Single-Crystal Diffractometry Methods in the Analysis of Protonation Pathways of 2-Amino-4-benzylsulfanyl-6-methylpyrimidines》 about this compound( cas:6307-44-4 ) in Russian Journal of General Chemistry. Keywords: aminomethyl pyrimidinethione benzyl chloride protonation mechanism NMR chem shift. We’ll tell you more about this compound (cas:6307-44-4).

Protonation pathways of 2-amino-4-benzylsulfanyl-6-methylpyrimidines have been investigated by means of semiempirical PM3 quantum-chem. simulation, 13C NMR spectroscopy, and single-crystal diffractometry methods. In the gas phase and in the bipolar aprotic solvent, the protonation involves the N1 atom. The protonation in the crystalline state is characterized by the formation of a branched system of H-bonds, involving the protons of the amino group besides the mentioned nitrogen atom.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Product Details of 119639-24-6. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation. Author is Park, Hojoon; Yu, Jin-Quan.

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

Application In Synthesis of 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: Synthesis and structure-activity relationships of a peptide scaffold. Author is Yue, Eddy W.; Wayland, Brian; Douty, Brent; Crawley, Matthew L.; McLaughlin, Erin; Takvorian, Amy; Wasserman, Zelda; Bower, Michael J.; Wei, Min; Li, Yanlong; Ala, Paul J.; Gonneville, Lucie; Wynn, Richard; Burn, Timothy C.; Liu, Phillip C. C.; Combs, Andrew P..

Oxo- and trioxo-substituted isothiazolidinylphenylalanines are prepared as tyrosine mimetics by Suzuki coupling reactions of chloroisothiazolidinones and chlorodioxoisothiazolidinones with N-Boc-4-borono-L-phenylalanine derivatives; the isothiazolidinylphenylalanines (with or without subsequent hydrogenation) are incorporated into dipeptides prepared as human protein tyrosine phosphatase 1B (PTP1B) inhibitors such as I. Of the compounds tested, I is the most potent inhibitor of PTP1B with an IC50 value of 40 nM; the corresponding mixture of isothiazolidinone diastereomers inhibits PTP1B with an IC50 value of 80 nM, and the separated (R)-isothiazolidinone diastereomer inhibits PTB1B with an IC50 value of 15.5 μM; the related dipeptides prepared inhibit PTP1B less potently than either I or the mixture of isothiazolidine diastereomers containing I. Crystal structures of a dioxothiazolidinone-substituted dipeptide and a dioxoisothiazolinone-substituted dipeptide bound to PTP1B are determined by X-ray crystallog.; the low energy conformation found by ab initio calculations for the saturated heterocycle more closely approaches the conformation obtained upon binding to PTP1B than that of the unsaturated heterocycle.

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Reference:
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.Abou-Gharbia, Magid; Moyer, John A.; Patel, Usha; Webb, Michael; Schiehser, Guy; Andree, Terrance; Haskins, J. Thomas researched the compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide( cas:119639-24-6 ).COA of Formula: C7H11NO3S.They published the article 《Synthesis and structure-activity relationship of substituted tetrahydro- and hexahydro-1,2-benzisothiazol-3-one 1,1-dioxides and thiadiazinones: potential anxiolytic agents》 about this compound( cas:119639-24-6 ) in Journal of Medicinal Chemistry. Keywords: piperazinylbutylbenzisothiazolone preparation anxiolytic structure activity; piperazinylbutylthiadiazinone dioxide preparation anxiolytic; benzisothiazolone piperazinylbutyl dioxide preparation anxiolytic; thiadiazinone piperazinylbutyl dioxide preparation anxiolytic. We’ll tell you more about this compound (cas:119639-24-6).

Several novel substituted tetrahydro- and hexahydro-1,2-benzisothiazole-3-one 1,1-dioxides, e.g., I [X = CH:CH, R = 2-pyrimidinyl (II); X = CH2, R = 3-C6H4CF3 (III)], IV (R = 2-pyrazinyl), and thiadiazinones V (R = 2-pyrimidinyl, 6-chloro-2-pyrazinyl) were prepared and examined in a series of in vitro and in vivo tests to determine their pharmacol. profile. Most compounds were orally active in blocking the conditioned avoidance response (CAR) but did not antagonize apomorphine-induced stereotyped behavior. Several compounds demonstrated moderate to high affinity for the 5-HT1A receptor binding site, with II and III containing 2-pyrimidinylpiperazinyl and [3-(trifluoromethyl)phenyl]piperazinyl moieties and IV containing the 2-pyrazinylpiperazinyl moiety displaying the highest affinity (K2 values of 10, 4, and 9 nM, resp. II, buspirone, and ipsapirone showed similarities in their neurochem. and behavioral profiles. They were similar in potency in blocking CAR with AB50 values of 39, 32, and 42 mg/kg, resp. They also demonstrated high affinity and selectivity for the 5-HT1A receptor site (Ki = 10 nM) and exhibited partial agonist/antagonist activity in the serotonin syndrome test. In addition, II inhibited apomorphine-induced climbing behavior much more potently (ED50 of 3.4 mg/kg) than stereotyped behavior (ED50 of 32.2 mg/kg) and will be evaluated further. Structure-activity relationships within this series of compounds are discussed.

Although many compounds look similar to this compound(119639-24-6)COA of Formula: C7H11NO3S, numerous studies have shown that this compound(SMILES:O=C(C=C1)N(C(C)(C)C)S1(=O)=O), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Park, Hojoon; Yu, Jin-Quan published the article 《Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation》. Keywords: palladium catalyzed cycloaddition carbon hydrogen bond activation; amide lactam cycloaddition maleimide.They researched the compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide( cas:119639-24-6 ).Name: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:119639-24-6) here.

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.

Although many compounds look similar to this compound(119639-24-6)Name: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, numerous studies have shown that this compound(SMILES:O=C(C=C1)N(C(C)(C)C)S1(=O)=O), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

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, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Organic Letters called Cross-Coupling of Mesylated Phenol Derivatives with Potassium Ammonio- and Amidomethyltrifluoroborates, Author is Molander, Gary A.; Beaumard, Floriane, which mentions a compound: 1268340-93-7, SMILESS is F[B-](F)(C[NH+]1CCCCC1)F, Molecular C6H13BF3N, COA of Formula: C6H13BF3N.

A large array of aryl and heteroaryl mesylates have been successfully employed as electrophiles in a Csp2-Csp3 Suzuki-Miyaura cross-coupling with potassium ammonio- and amidomethyltrifluoroborates to afford the corresponding products in high yields.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Yue, Eddy W.; Wayland, Brian; Douty, Brent; Crawley, Matthew L.; McLaughlin, Erin; Takvorian, Amy; Wasserman, Zelda; Bower, Michael J.; Wei, Min; Li, Yanlong; Ala, Paul J.; Gonneville, Lucie; Wynn, Richard; Burn, Timothy C.; Liu, Phillip C. C.; Combs, Andrew P. published the article 《Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: Synthesis and structure-activity relationships of a peptide scaffold》. Keywords: isothiazolidinylphenylalanine preparation; isothiazolidine containing dipeptide amide preparation protein tyrosine phosphatase inhibitor; structure isothiazolidine containing dipeptide amide inhibition PTP1B; mol crystal structure PTP1B bound isothiazolidine containing dipeptide amide; conformation isothiazolidine containing dipeptide amide ab initio calculation.They researched the compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide( cas:119639-24-6 ).Category: isothiazole. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:119639-24-6) here.

Oxo- and trioxo-substituted isothiazolidinylphenylalanines are prepared as tyrosine mimetics by Suzuki coupling reactions of chloroisothiazolidinones and chlorodioxoisothiazolidinones with N-Boc-4-borono-L-phenylalanine derivatives; the isothiazolidinylphenylalanines (with or without subsequent hydrogenation) are incorporated into dipeptides prepared as human protein tyrosine phosphatase 1B (PTP1B) inhibitors such as I. Of the compounds tested, I is the most potent inhibitor of PTP1B with an IC50 value of 40 nM; the corresponding mixture of isothiazolidinone diastereomers inhibits PTP1B with an IC50 value of 80 nM, and the separated (R)-isothiazolidinone diastereomer inhibits PTB1B with an IC50 value of 15.5 μM; the related dipeptides prepared inhibit PTP1B less potently than either I or the mixture of isothiazolidine diastereomers containing I. Crystal structures of a dioxothiazolidinone-substituted dipeptide and a dioxoisothiazolinone-substituted dipeptide bound to PTP1B are determined by X-ray crystallog.; the low energy conformation found by ab initio calculations for the saturated heterocycle more closely approaches the conformation obtained upon binding to PTP1B than that of the unsaturated heterocycle.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com