Tag: M.W:100-200

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 Discovery of 5-substituent-N-arylbenzamide derivatives as potent, selective and orally bioavailable LRRK2 inhibitors, published in 2017-09-01, which mentions a compound: 22353-34-0, Name is 5-Chloropyridin-3-amine, Molecular C5H5ClN2, Synthetic Route of C5H5ClN2.

Leucine-rich repeat kinase 2 (LRRK2) has been suggested as a potential therapeutic target for Parkinson’s disease. Herein we report the discovery of 5-substituent-N-arylbenzamide derivatives as novel LRRK2 inhibitors. Extensive SAR study led to the discovery of compounds I, which demonstrated potent LRRK2 inhibition activity, high selectivity across the kinome, good brain exposure, and high oral bioavailability.

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

Synthetic Route of C11H13OP. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about A chiral shift reagent for measurement of optical purities of chiral phosphine oxides. Author is Zhou, Zhenhua.

(R)-(-)-N-(3,5-Dinitrobenzyl)-α-phenylethylamine (I) is an excellent chiral shift reagent for measurement of optical purities of chiral phosphine oxides. The method of preparation and application of reagent I are discussed in detail. 1-Phenyl-3-methyl-2-phospholene(II) is oxidized to 1-phenyl-3-methyl-2-phospholene 1-oxide (III) which is then reacted with tert-BuOOH with complete retention of optical activity. When phosphine oxide is mixed with reagent(I), optical purity of phosphine oxide can be measured according to 1H NMR spectra; the optical purity of II can be determined

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《An efficient approach towards the stereospecific synthesis of epoxides from phospholene oxides》. Authors are Yamashita, Mitsuji; Krishna Reddy, Valluru; Rao, Lakonda Nagaprasada; Haritha, Buchammagari; Maeda, Motoki; Suzuki, Keiji; Totsuka, Hirono; Takahashi, Masaki; Oshikawa, Tatsuo.The article about the compound:4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxidecas:707-61-9,SMILESS:CC1=CP(CC1)(C2=CC=CC=C2)=O).Recommanded Product: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide. Through the article, more information about this compound (cas:707-61-9) is conveyed.

A novel method has been developed for stereospecific conversion of 2-phospholene 1-oxides into their corresponding 2,3-epoxides in high yields using sodium peroxide as a reagent. 2,3-Dihydro-1-phenyl-1H-phosphole 1-oxide (I) was inert to oxidation with 3-chloroperbenzoic acid; oxidation of I with bromine or N-bromoacetamide gave 2-bromo-3-hydroxy-1-phenylphospholane oxide as diastereomeric mixture and subsequent treatment of the bromohydrin gave a mixture of (1R,2S,5S)-rel-2-phenyl-6-Oxa-2-phosphabicyclo[3.1.0]hexane 2-oxide (erythro, II) and (1R,2R,5S)-rel-2-phenyl-6-Oxa-2-phosphabicyclo[3.1.0]hexane 2-oxide (threo). Epoxidation of I using sodium peroxide [Na2(O2)] gave II as a single diastereomer in 76% yield. 2,3-Dihydro-4-methyl-1-phenyl-1H-phosphole 1-oxide and 2,3-dihydro-1-methoxy-4-methyl-1H-phosphole 1-oxide failed to react with sodium peroxide [Na2(O2)]. The compounds thus prepared are intermediates for AZT analogs of phospha sugars (no data).

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

Electric Literature of C4H7BrO2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Bromomethyl-1,3-dioxolane, is researched, Molecular C4H7BrO2, CAS is 4360-63-8, about Unexpected Formation of Thiophene in the Pyrrole Synthesis from Methoxyallene and Methyl Isothiocyanate. Author is Tarasova, O. A.; Nedolya, N. A.; Albanov, A. I.; Trofimov, B. A..

The sequential reaction of lithiated methoxyallene, Me isothiocyanate, and 2-(bromomethyl)-1,3-dioxolane in the presence of CuBr yields a 2,3-disubstituted thiophene instead of the expected pyrrole. The process was accomplished in one preparative stage and involved intramol. cyclization of the in situ-generated lithium allenylimidothioate and N-alkylation of the resulting lithium thienylamide. Varying the reaction conditions did not affect its route: in all cases, the only product was N-(1,3-dioxolan-2-ylmethyl)-3-methoxy-N-methylthiophen-2-amine.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Bromomethyl-1,3-dioxolane( cas:4360-63-8 ) is researched.Recommanded Product: 2-Bromomethyl-1,3-dioxolane.Li, Yaoqi; Sun, Zhihua published the article 《Synthesis of lesinurad via a multicomponent reaction with isocyanides and disulfides》 about this compound( cas:4360-63-8 ) in Heterocycles. Keywords: Lesinurad preparation. Let’s learn more about this compound (cas:4360-63-8).

An efficient synthesis of Lesinurad I, a selective uric acid reabsorption inhibitor was developed via reaction starting from 4-cyclopropylnaphthalen-1-amine hydrochloride. The route to synthesis of compound I avoided the use of thiophosgene and the formation of thiols. The key reaction in this synthesis was construction of the 1,2,4-triazole ring in 72% yield. Compound I is obtained in 45% yield over 5 steps.

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2- and 5-Fluoronicotinic acids》. Authors are Beaty, R. D.; Musgrave, W. K. R..The article about the compound:Methyl 5-fluoro-3-pyridinecarboxylatecas:455-70-9,SMILESS:COC(=O)C1=CC(F)=CN=C1).HPLC of Formula: 455-70-9. Through the article, more information about this compound (cas:455-70-9) is conveyed.

5-Aminonicotinic acid (I) (3 g.) in 20 cc. 40% HBF4 at -5° treated with 2.5 g. NaNO2, the mixture kept 1 h., heated 30 min. at 50°, neutralized with Na2CO3, and the resulting salt refluxed 2-3 h. with 3% MeOH-H2SO4, gives 0.3 g. Me 5-fluoronicotinate, m. 48°. The 2-isomer of I (2 g.) in 10 cc. 40% HBF4, diazotized with 1 g. NaNO2 in 10 cc. H2O at 0 to -5°, and the solution kept 1 h. at 0°, heated 1 h. at 50-60°, and basified to pH 5 with NaOH, gives 33% 2-fluoronicotinic acid, m. 164-5°; the Me ester m. 74-5° and the amide m. 124°. 3-Fluoropicolinic acid could not be prepared by this method.

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

Quality Control of 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Improved syntheses and characterization of the isomers of 3-methyl-1-phenylphospholene 1-oxide. Author is Moedritzer, Kurt; Miller, Raymond E..

Isomerically pure 3-methyl-1-phenyl-2-phospholene 1-oxide and 3-methyl-1-phenyl-3-phospholene 1-oxide were prepared and characterized by 1H (60 and 270 MHz), 31P and 13C NMR, IR, Laser Raman, and mass spectrometry. 1,4-Cycloaddition of isoprene and PhPCl2 after hydrolysis of the addition product, yielded a mixture of the above 2-isomer and small amounts of 3-isomer from which pure 2-isomer was separated by fractional crystallization The analog reaction with PhPBr2 gave isomerically pure 3-isomer. An improved and shortened work-up procedure for the phospholene oxides was used resulting in higher yields.

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

Kim, Dae-Kwon; Um, Hyun-Suk; Park, Hoyoon; Kim, Seonwoo; Choi, Jin; Lee, Chulbom published an article about the compound: 2-Bromomethyl-1,3-dioxolane( cas:4360-63-8,SMILESS:BrCC1OCCO1 ).Category: dioxole. 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:4360-63-8) through the article.

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives RS(O)2R1 (R = 3-phenylpropyl, Ph, naphthalen-2-yl, etc.; R1 = [(tert-butyldimethylsilyl)oxy]methyl, 4-(morpholin-4-yl)phenyl, hex-5-yn-1-yl, etc.) has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent TBSOMS-Na, easily prepared from the com. reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles R1X (X = I, Br). The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a sep. unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Structure of diene-phosphonous dihalide addition products and of derived phospholenes and phospholene oxides》. Authors are Quin, Louis D.; Gratz, Joan P.; Barket, Thomas P..The article about the compound:4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxidecas:707-61-9,SMILESS:CC1=CP(CC1)(C2=CC=CC=C2)=O).Related Products of 707-61-9. Through the article, more information about this compound (cas:707-61-9) is conveyed.

The cycloadducts of MePCl2 and butadiene, isoprene, 3,4-dimethylbutadiene, or piperylene give rise to 3-phospholene oxides on hydrolysis and 3-phospholenes (I) on reduction with Mg. The cycloadduct from butadiene also contained the 3-phospholene ring. The 3-phospholene oxides may be caused to rearrange to 2-phospholene oxides either thermally or by refluxing aqueous base. Acid treatment was effective only for rearranging the 3-Me derivative The 3,4-di-Me derivative resisted rearrangement conditions. PhPBr2 (synthesized by a new method from PhP(O)(OH)Cl and PBr3) also gave an adduct with isoprene shown by N.M.R. studies to contain the 3-phospholene ring, which was preserved in the oxide and phospholene. However, the isoprene-PhPCl2 adduct contained the 2-phospholene ring; the derived oxide and phospholene were also the 2-isomers. Independent syntheses of the isomeric 1-phenyl-3-methylphospholene oxides confirmed the assignments. The adduct from piperylene and PhPBr2 also gave on hydrolysis the 3-phospholene oxide, while that from PhPCl2 gave the 2-isomer. 26 references.

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

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: 707-61-9, is researched, SMILESS is CC1=CP(CC1)(C2=CC=CC=C2)=O, Molecular C11H13OPJournal, Article, Journal of the American Chemical Society called A Phosphetane Catalyzes Deoxygenative Condensation of α-Keto Esters and Carboxylic Acids via PIII/PV=O Redox Cycling, Author is Zhao, Wei; Yan, Patrick K.; Radosevich, Alexander T., the main research direction is phosphetane catalyst preparation oxygenative condensation ketoester carboxylic acid.Application of 707-61-9.

A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV=O cycling. The importance of ring strain in the phosphacyclic catalyst is substantiated by an observed temperature-dependent product selectivity effect. The results point to an inherent distinction in design criteria for organophosphorus-based catalysts operating via PIII/PV=O redox cycling as opposed to Lewis base (nucleophilic) catalysis.

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