Tag: M.W=100-200

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis and properties of 2,4-diaminothiazoles》. Authors are Davies, W.; Maclaren, J. A.; Wilkinson, L. R..The article about the compound:Thiazole-2,4-diamine hydrochloridecas:72792-54-2,SMILESS:NC1=NC(N)=CS1.[H]Cl).Application In Synthesis of Thiazole-2,4-diamine hydrochloride. Through the article, more information about this compound (cas:72792-54-2) is conveyed.

CS(NH2)2 (I) and ClCH2CN (1 mol. each) in 15 parts MeOH, kept 3 weeks at room temperature or 1 week at 35°, give a nearly quant. yield of 2,4-diaminothiazole (II) HCl salt (III), m. above 360°; EtOH can be used as the solvent [a good yield of III results on refluxing 4 hrs.]; with Me2CO as the solvent, an oil gradually seps. and slowly crystallizes, yielding III; with N NaOH III yields II, m. 143° (decomposition). II yields a picrate, m. 233° (decomposition) (Land, et al., C.A. 41, 412i, gave above 350°). III (3.4 g.) in 10 cc. H2O, treated with 8 cc. 10% NaOH and then with 4 cc. Ac2O, gives 58% of 2,4-diacetamidothiazole, m. 240-1°, unchanged by boiling Ac2O in C5H5N, does not form a picrate. I and PhCHBrCN in EtOH (6 days at 35° or 6 hrs. on the water bath) give 83% of the HBr salt (IV), m. above 250° (decomposition), of 2,4-diamino-5-phenylthiazole (V), m. 163-4° (decomposition); picrate, yellow, m. 189-91° (decomposition). IV (2.7 g.), warmed with 1 cc. C5H5N, cooled, and treated with 10 cc. Ac2O (6 days at room temperature), gives 69% of the 2,4-di-Ac derivative (VI)of V, m. 233-4° [picrate (VII), yellow, m. 203-7° (decomposition)]. IV (5.4 g.), 2 cc. C5H5N, and 20 cc. Ac2O, refluxed 1 hr., give 92% 2,4-diacetamido-3-acetyl-5-phenylthiazole (VIII), m. 193-4.5°; VIII results on refluxing VI 1 hr. in Ac2O; refluxed 6 hrs. in 20% EtOH or treated 12 hrs. at room temperature with EtOH containing 0.33 ml. 10% NaOH, VIII yields VI; alc. picric acid gives VII. I (3.8 g.) and 4.5 g. MeCHClCN in 50 cc. 96% EtOH, kept 10 weeks at 40°, give 51% 2,4-diamino-5-methylthiazole (IX) HCl salt (X), m. 229-31° (decomposition); X results in 40% yield by refluxing the reactant 20 hrs. in EtOH. Mol. quantities of I, MeCHClCN, and NaI in EtOH, 3 months at room temperature, give 75% of the HI salt (XI) of IX, cream, m. 225° (decomposition); the yield is 72% on boiling the solution 10 hrs. X or XI with NaOH or NH4OH gives 2-amino-4-hydroxy-5-methylthiazole, m. 207-8° (decomposition); this results also on refluxing I and MeCHClCONH2 9 hrs. in EtOH. X is unchanged on heating with concentrated HCl on the water bath; 14 N H2SO4 gives an alkali-soluble oil (probably 2,4-dihydroxy-5-methylthiazole). IX picrate, orange, m. 216-17°; di-Ac derivative of IX, m. 23°. I and Me2CBrCN [MeCH(CN)CH2Cl] do not react on refluxing 13 hrs. in EtOH; PhNHCSNH2 and ClCH2CN, refluxed 1 hr. and kept 3 weeks at room temperature, give a small quantity of 4-hydroxy-2-anilinothiazole. CO(NH2)2 does not react with ClCH2CN (1 month at room temperature or refluxed 16 hrs.). CSe(NH2)2 (1.3 g.) and 0.7 g. ClCH2CN in 20 cc. EtOH, refluxed 2.5 hrs., give 0.8 g. 2,4-diaminoselenazole-HCl, does not m. at 250°, slowly deposits Se from hot aqueous-alc. solution; picrate, golden, m. 220-5°. III (0.5 g.) in 7.5 cc. H2O, refluxed 6 hrs., give 85% 2-amino-4-hydroxythiazole, m. 230-40° (decomposition); 1.5 g. III, 10 cc. H2O, and 5 cc. concentrated HCl, refluxed 5 hrs., give 2,4-dihydroxythiazole (XII). IV (5% aqueous solution), refluxed 3 hrs., gives 2-amino-4-hydroxy-5-phenyl thiazole, m. 229-30° [also formed (58% yield) from 5.6 g. PhCHBrCONH2 and 1.5 g. I in 50 cc. boiling EtOH (2.5 hrs.)]; picrate, m. 204°. Prepared in a similar manner to XII, but refluxed only 2 hrs., 2,4-dihydroxy-5-phenylthiazole m. 130-1°; it results also on refluxing 1 g. VI or VIII with 10 cc. 6 N HCl. H2NCS2NH4 (1.5 g.) and 2.2 g. PhNHCO2Et in 20 cc. 75% EtOH, 1 month at 35-40°, give 0.1 g. 5-benzylidenerhodanine, m. 203-4°; however, ClCH2CN gives only NH4Cl and S-containing indefinite liquids, which are also obtained with MeCSNH2, H2NCS2CH2Ph, or H2NCSNHCH2CH:CH2. V is a very potent analeptic but IX is without action.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol( cas:35836-73-8 ) is researched.Recommanded Product: 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol.McLaughlin, Mark L.; McKinney, Jeffrey A.; Paquette, Leo A. published the article 《Chemistry of isodicyclopentadienes. Part 36. Efficient preparation of homochiral bicyclo-annulated cyclopentadienes via the Skatteboel rearrangement. Avoidance of limitations due to angle strain》 about this compound( cas:35836-73-8 ) in Tetrahedron Letters. Keywords: cyclopentadiene annulation nopol camphor. Let’s learn more about this compound (cas:35836-73-8).

(1R)-(-)-Nopol and (1R)-(+)-camphor are both vinylated in 2 steps to give vinylbicycloheptenes I and II. Dibromocyclopropanation followed by carbene formation with MeLi leads to optically pure annulated cyclopentadienes in ∼40% overall yield.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensation reaction of amino alcohols with imides. IV. Condensation products of β-(cycloamino)ethanols with succinimide and with phthalimide-formation of β-(cycloamino)ethylamines》. Authors are Nakajima, Kazuo.The article about the compound:2-(3,4-Dihydroquinolin-1(2H)-yl)ethanaminecas:37481-18-8,SMILESS:NCCN1CCCC2=C1C=CC=C2).Application of 37481-18-8. Through the article, more information about this compound (cas:37481-18-8) is conveyed.

cf. CA 57, 8545h. Seven aminoalcs. (RNCH2CH2OH) (I), where RN = (CH2)4N (a), (CH2)5N (b), β-tetrahydroquinoline (c), morpholino (d), 4-ethylpiperazino (e), 4-butylpiperazino (f), and 4-phenylpiperazino (g). I and phthalimide heated at 200° while removing the H2O formed yielded RNCH2CH2N(CO)2C6H4-o (II) (RN, m.p., b10, m.p. of picrate, and decomposition point of Pt salt given): a, 109°, 220°, 218°, 212°; b, 90°, 206°, 215°, 215°; c, 137°, 273°, 144°, 204°; d, 135°, 216°, 232°, 146°; e, 115°, 227°, 245° (decomposition), 265°; f, 75°, 252°, 260° (decomposition), 271°; g, 158°, 279°, 218° (decomposition), 262°. Similarly, I and succinimide yielded RNCH2CH2N(COCH2)2 (III) (RN, m.p., b10, m.p. of picrate, and decomposition point of Pt salt given): a, 55°, 170°, 158°, 212°; b, -, 170°, 190°, 230°; c, 115°, 210°, 180°, -; d, 75°, 170°, 181°, 175°; e, -, 199°, 245°, 245°; f, 65°, 223°, 225°, 255°; g, 141°, 272°, 175°, 236°. II and III refluxed with 20% HCl 3-5 hrs., phthalic acid or succinic acid filtered off, and the filtrate concentrated yielded RNCH2CH2NH2.HCl (IV.HCl). Free RNCH2CH2NH2 (IV) was obtained by a long extraction of neutralized IV.HCl with ether. (RN, b10, b760, m.p. of picrate, and decomposition point of Pt salt given) a, 33°, 165-6°, 210° (decomposition), 207°; b, 50°, 185°, ∼200 (decomposition), 218°; c, 157°, 290°, -, -; d, 81°, 204°, 177° (decomposition), 237°; e, 88°, 223-4°, 230°, 270°; f, 120°, 255°, 116°, 252°; g, (m. 80°), 191°, 326°, -. 210-40°.

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Recommanded Product: 4144-22-3. 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: 1-(tert-Butyl)-1H-pyrrole-2,5-dione, is researched, Molecular C8H11NO2, CAS is 4144-22-3, about A 2-(1-methylhydrazinyl)pyridine-directed C-H functionalization/spirocyclization cascade: facile access to spirosuccinimide derivatives. Author is Zhao, Hua; Shao, Xiaoru; Wang, Taimin; Zhai, Shengxian; Qiu, Shuxian; Tao, Cheng; Wang, Huifei; Zhai, Hongbin.

A cobalt-catalyzed oxidative coupling of benzoic hydrazides with maleimides by utilizing 2-(1-methylhydrazinyl)pyridine as a bidentate directing group has been developed. This C-H functionalization/spirocyclization cascade protocol shows high efficiency and remarkable functional group tolerance, and the ubiquitous spirosuccinimides were obtained in good to excellent yields with high regioselectivity. This strategy also provides a novel and efficient access to diverse sym. and unsym. bisspirosuccinimides.

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Application In Synthesis of 2-(3,4-Dihydroquinolin-1(2H)-yl)ethanamine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-(3,4-Dihydroquinolin-1(2H)-yl)ethanamine, is researched, Molecular C11H16N2, CAS is 37481-18-8, about Structure-Activity Relationship for Small Molecule Inhibitors of Nicotinamide N-Methyltransferase. Author is Neelakantan, Harshini; Wang, Hua-Yu; Vance, Virginia; Hommel, Jonathan D.; McHardy, Stanton F.; Watowich, Stanley J..

Nicotinamide N-methyltransferase (NNMT) is a fundamental cytosolic biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small mol. inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure-activity relationships (SARs) for NNMT inhibitors. Screening of N-methylated quinolinium, isoquinolinium, pyrididium, and benzimidazolium/benzothiazolium analogs resulted in the identification of quinoliniums as a promising scaffold with very low micromolar (IC50 ∼ 1 μM) NNMT inhibition. Computer-based docking of inhibitors to the NNMT substrate (nicotinamide)-binding site produced a robust correlation between ligand-enzyme interaction docking scores and exptl. calculated IC50 values. Predicted binding orientation of the quinolinium analogs revealed selective binding to the NNMT substrate-binding site residues and essential chem. features driving protein-ligand intermol. interactions and NNMT inhibition. The development of this new series of small mol. NNMT inhibitors direct the future design of lead drug-like inhibitors to treat several metabolic and chronic disease conditions characterized by abnormal NNMT activity.

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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: 4144-22-3, is researched, Molecular C8H11NO2, about One-pot Synthesis of Oxindoles through C-H Alkylation and Intramolecular Cyclization of Azobenzenes with Internal Olefins, the main research direction is azobenzene alkene dicarbonyl rhodium alkylation catalyst; alkylated azobenzene regioselective preparation zinc reductive intramol cyclization; oxindole preparation.SDS of cas: 4144-22-3.

The rhodium(III)-catalyzed site-selective C-H alkylation of azobenzenes and internal olefins, such as maleimides, maleates and fumarates, followed by reductive intramol. cyclization is described. A cationic rhodium catalyst in the presence of acetic acid additive in dichloroethane solvent was found to be the optimal catalytic system for the construction of ortho-alkylated azobenzenes, which smoothly underwent the intramol. cyclization leading to the formation of C3-functionalized oxindoles I (X = NH, O; R1 = H, 2-Me, 2-Et, 4-Me, etc.;R2 = Me, Et, Bn, n-Bu, etc.) in the presence of zinc powder and acetic acid. The formed oxindole scaffold could be an important asset towards the development of novel bioactive compounds

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(3,4-Dihydroquinolin-1(2H)-yl)ethanamine, is researched, Molecular C11H16N2, CAS is 37481-18-8, about Discovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays, the main research direction is food intake reduction 5HT2C receptor agonists lead; 5-HT(2C) receptor; Agonist; GPCR; Lead identification.Recommanded Product: 37481-18-8.

A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clin. studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.

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Chlorides – an overview | ScienceDirect Topics

HPLC of Formula: 4144-22-3. 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: 1-(tert-Butyl)-1H-pyrrole-2,5-dione, is researched, Molecular C8H11NO2, CAS is 4144-22-3, about Rhodium(III)-Catalyzed Diastereoselective Synthesis of 1-Aminoindanes via C-H Activation. Author is Han, Sang Hoon; Mishra, Neeraj Kumar; Jeon, Mijin; Kim, Saegun; Kim, Hyung Sik; Jung, Seung-Young; Jung, Young Hoon; Ku, Jin-Mo; Kim, In Su.

In the presence of [Cp*RhCl2]2, AgSbF6, and LiOAc, N-tosylbenzaldimines such as I underwent C-H activation and diastereoselective cycloaddition reactions with maleimides, α,β-unsaturated esters and ketones, and nitroalkenes to yield indanamines such as II in 22-96% yields and as single diastereomers in all but one case.

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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: 35836-73-8, is researched, Molecular C11H18O, about Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes, the main research direction is terpene preparation homologation Matteson reaction flow chem.Application In Synthesis of 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol.

The Matteson reaction is ideally suited for flow chem. since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative workup. The new terpene alcs. are validated with respect to their olfactoric properties.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 1-(tert-Butyl)-1H-pyrrole-2,5-dione, is researched, Molecular C8H11NO2, CAS is 4144-22-3, about An Approach to 3-(Indol-2-yl)succinimide Derivatives by Manganese-Catalyzed C-H Activation, the main research direction is crystal mol structure phenyl pyridinyl indolyl pyrrolidinedione; manganese catalyzed addition indole maleimide functional group compatibility.Application In Synthesis of 1-(tert-Butyl)-1H-pyrrole-2,5-dione.

The manganese-catalyzed addition of C-2 position of indoles to maleimides has been achieved under additive-free conditions. The manganese catalyst exhibits excellent chemo- and regioselectivity, good functional group compatibility, and high catalytic efficiency. The substrate scope can also be extended to maleates, Et acrylate, 1,4-dihydro-1,4-epoxynaphthalene, pyrroles, and 2-phenylpyridine, which further demonstrates the universality of this straightforward approach.

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