28657-75-2 | Page 2 of 3 | Dioxole related

Parveen, Naziya et al. published their research in Advanced Synthesis & Catalysis in 2019 | CAS: 28657-75-2

1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Product Details of 28657-75-2

Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction was written by Parveen, Naziya;Sekar, Govindasamy. And the article was included in Advanced Synthesis & Catalysis in 2019.Product Details of 28657-75-2 This article mentions the following:

An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones I (R¹ = H, 6-Br, 6-Ph, 6-PhCC, 5,6-OCH₂O; R² = Ph, 4-MeOC₆H₄, 3-furyl, 2-indolyl, etc.) from 2′-iodochalcones II via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst is described. An immense array of indanones I using both electron-rich and electron-deficient 2′-iodochalcones was synthesized. Further derivatization of the indanone I (R¹ = H; R² = Ph) was achieved successfully. The heterogeneous nature of the Pd-BNP was validated by centrifugation test and mercury poisoning experiment Pd-BNP was successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles was confirmed by TEM anal. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Product Details of 28657-75-2).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Kothandaraman, Prasath et al. published their research in Tetrahedron in 2013 | CAS: 28657-75-2

Metal-free synthesis of 1H-indole-2-carbaldehydes by N-iodosuccinimide-mediated cyclization of 1-(2′-anilinyl)prop-2-yn-1-ols in water. A formal synthesis of (R)-calindol was written by Kothandaraman, Prasath;Lauw, Sherman Jun Liang;Chan, Philip Wai Hong. And the article was included in Tetrahedron in 2013.Application In Synthesis of 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone This article mentions the following:

A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2-carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn-1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yields (48-91%) from a wide range of alc. substrates that are low cost, easily accessible, and ecol. benign. The utility of the approach as a potential scale-up strategy for the synthesis of the indole was exemplified by the large-scale synthesis of one example in an excellent yield. The synthetic utility of this chem. was also demonstrated in a formal synthesis of (R)-calindol. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Application In Synthesis of 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Li, Leping et al. published their research in Journal of Medicinal Chemistry in 1994 | CAS: 28657-75-2

Antitumor Agents 155. Synthesis and Biological Evaluation of 3′,6,7-Substituted 2-Phenyl-4-quinolones as Antimicrotubule Agents was written by Li, Leping;Wang, Hui-Kang;Kuo, Sheng-Chu;Wu, Tian-Shung;Mauger, Anthony;Lin, Chii M.;Hamel, Ernest;Lee, Kuo-Hsiung. And the article was included in Journal of Medicinal Chemistry in 1994.Reference of 28657-75-2 This article mentions the following:

A series of 3′,6,7-substituted 2-phenyl-4-quinolones were designed and synthesized as antimitotic antitumor agents. All compounds showed cytotoxic effects (log GI₅₀ ≤ -4.0; log drug molar concentration required to cause 50% inhibition) against the growth of a variety of human tumor cell lines, including those derived from solid tumors such as non-small cell lung, colon, central nervous system, ovary, prostate, and breast cancers, when evaluated in the National Cancer Institute’s 60 human tumor cell line in vitro screen. The most potent compound (I) demonstrated strong cytotoxic effects with GI₅₀ values in the nanomolar or subnanomolar range in almost all the tumor cell lines. Compound I was also a potent inhibitor of tubulin polymerization and radiolabeled colchicine binding to tubulin, with activity comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Reference of 28657-75-2).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Martinez, Ricardo et al. published their research in Tetrahedron in 2006 | CAS: 28657-75-2

Easy α-alkylation of ketones with alcohols through a hydrogen autotransfer process catalyzed by RuCl₂(DMSO)₄ was written by Martinez, Ricardo;Ramon, Diego J.;Yus, Miguel. And the article was included in Tetrahedron in 2006.Application of 28657-75-2 This article mentions the following:

The electrophilic α-alkylation of ketones with alcs. is accomplished by a hydrogen autotransfer process catalyzed by RuCl₂(DMSO)₄. The reaction can produce either simple alkylated ketones or α,β-unsaturated ketones just by choosing the appropriate starting ketones (Me ketones or bicyclic methylenic ketones, resp.), as well as quinolines (by using 2-aminobenzyl alc. derivatives) or the corresponding alc. derivatives by the addition of an extra equivalent of the initial alc. In the last case, after the above alkylation process reduction of the carbonyl compound takes place. A mechanistic study seems to indicate that the process goes through the oxidation of the alcs. with ruthenium (after a previous deprotonation) to yield the corresponding aldehyde and a ruthenium hydride intermediate. In turn, the aldehyde suffers a classical aldol reaction with the starting ketone to form the α,β-unsaturated ketone, which finally is reduced through a Michael-type addition by the aforementioned ruthenium hydride intermediate. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Application of 28657-75-2).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Madhav, Bandaru et al. published their research in Helvetica Chimica Acta in 2010 | CAS: 28657-75-2

An Improved Protocol for the Synthesis of Quinoline-2,3-dicarboxylates under Neutral Conditions via Biomimetic Approach was written by Madhav, Bandaru;Murthy, Sabbavarapu Narayana;Rao, Kakulapati Rama;Nageswar, Yadavalli Venkata Durga. And the article was included in Helvetica Chimica Acta in 2010.COA of Formula: C9H9NO3 This article mentions the following:

A mild and efficient protocol for synthesis of quinoline-2,3-dicarboxylates in aqueous medium under neutral conditions via heterocyclization of ortho-aminoaryl ketones with acetylenedicarboxylates is described. The reaction proceeded smoothly in H₂O catalyzed by supramol. catalyst β-CD. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2COA of Formula: C9H9NO3).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Filimonov, S. I. et al. published their research in Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya in 2005 | CAS: 28657-75-2

Synthesis of substituted 2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]diazepine-7-sulfamides was written by Filimonov, S. I.;Kravchenko, D. V.;Khakhina, M. Yu.;Dorogov, M. V.;Tkachenko, S. E.;Ivashchenko, A. V.. And the article was included in Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya in 2005.Category: dioxole This article mentions the following:

Liquid-phase parallel synthesis of a combinatorial library of 320 2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-sulfonamides I (R¹, R² = H, Me; R³R⁴N = primary or secondary aliphatic, cycloaliphatic, aromatic or heterocyclic amine) was carried out by chlorosulfonylation of the corresponding benzodiazepines followed by reaction with primary and secondary amines. The pharmacol. important parameters of some of these compounds (mol. weight, lipophilicity and number of hydrogen bond donor and acceptors) have been calculated In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Category: dioxole).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Zhu, Zhaofu et al. published their research in Huaxue Yanjiu Yu Yingyong in 2003 | CAS: 28657-75-2

Synthesis and characterization of 4-substituted ethyl 2-methyl-6,7-methylenedioxy-3-quinolinecarboxylate was written by Zhu, Zhaofu. And the article was included in Huaxue Yanjiu Yu Yingyong in 2003.COA of Formula: C9H9NO3 This article mentions the following:

Et 4-R-2-methyl-6,7-methylenedioxy-3-quinolinecarboxylate (R = Me, Et, Pr, or isopropyl) was prepared from benzodioxole by acylation, nitration, reduction, and condensation in a yield of 74-87%. The mol. structures were determined by IR, ¹H-NMR, and MS. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2COA of Formula: C9H9NO3).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Chen, Yen Ting et al. published their research in Bioorganic & Medicinal Chemistry in 2004 | CAS: 28657-75-2

Parallel synthesis of a library of bidentate protein tyrosine phosphatase inhibitors based on the α-ketoacid motif was written by Chen, Yen Ting;Seto, Christopher T.. And the article was included in Bioorganic & Medicinal Chemistry in 2004.Application In Synthesis of 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone This article mentions the following:

Protein tyrosine phosphatases (PTPases) regulate intracellular signal transduction pathways by controlling the level of tyrosine phosphorylation in cells. These enzymes play an important role in a variety of diseases including type II diabetes and infection by the bacterium Yersinia pestis, which is the causative agent of bubonic plague. This report describes the synthesis, using parallel solution-phase methods, of a library of 104 potential inhibitors of PTPases. The library members are based on the bis(aryl α-ketocarboxylic acid) motif that incorporates a carboxylic acid on the central benzene linker. This carboxylic acid was coupled with a variety of different aromatic amines through an amide linkage. The aromatic component of the resulting amides is designed to make contacts with residues that surround the active site of the PTPase. The library was screened against the Yersinia PTPase and PTP1B. Based upon the screening results, four members of the library were selected for further study. These four compounds were evaluated against the Yersinia PTPase, PTP1B, TCPTP, CD45, and LAR. Compound 14 has an IC₅₀ value of 590 nM against PTP1B and is a reversible competitive inhibitor. This affinity represents a greater than 120-fold increase in potency over compound 2, the parent structure upon which the library was based. A second inhibitor, compound 12, has an IC₅₀ value of 240 nM against the Yersinia PTPase. In general, the selectivity of the inhibitors for PTP1B was good compared to LAR, but modest when compared to TCPTP and CD45. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Application In Synthesis of 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Verma, Ajay et al. published their research in Organic Letters in 2016 | CAS: 28657-75-2

Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp³)-C(sp²) Bond: Synthesis of Substituted Benzoxazinones was written by Verma, Ajay;Kumar, Sangit. And the article was included in Organic Letters in 2016.Formula: C9H9NO3 This article mentions the following:

A transition metal (TM)-free practical synthesis of biol. relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp³)-C(sp²) bond employing iodine, sodium bicarbonate, and tert-Bu hydroperoxide in DMSO at 95 °C. Control experiments and D. Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl₂. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Formula: C9H9NO3).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Yonekura, Kyohei et al. published their research in Molecules in 2018 | CAS: 28657-75-2

Indium-catalyzed annulation of o-acylanilines with alkoxyheteroarenes: synthesis of heteroaryl[b]quinolines and subsequent transformation to cryptolepine derivatives was written by Yonekura, Kyohei;Shinoda, Mika;Yonekura, Yuko;Tsuchimoto, Teruhisa. And the article was included in Molecules in 2018.Synthetic Route of C9H9NO3 This article mentions the following:

An efficient method for the synthesis of heteroaryl[b]quinolines such as I [R = H, 4-OH, 2,3-di-MeO, etc.; R¹ = Me, i-Pr, Ph, etc.; X = N, S] was developed via annulation of o-acylanilines and MeO-heteroarenes using an indium Lewis acid as catalyst for tandem N-C and C-C bond formation. A series of indolo[3,2-b]quinolines was subsequently transformed to structurally unprecedented cryptolepine derivatives Mechanistic studies showed that the N-C bond formation was followed by the C-C bond formation. The indium-catalyzed annulation reaction thus started with the nucleophilic attack of the NH₂ group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an S_NAr fashion and thereby the N-C bond was formed. The resulting intermediate then cyclized and gave C-C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, provided the HA[b]Q after aromatizing dehydration. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Synthetic Route of C9H9NO3).

Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem