Heterocyclic Building Blocks-Pyrrolines

Fier, Patrick S.; Hartwig, John F. published the article 《Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction》. Keywords: carbon hydrogen fluorination pyridine diazine inspired classic amination.They researched the compound: 4-Chloro-2-fluoropyridine( cas:34941-92-9 ).Reference of 4-Chloro-2-fluoropyridine. 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:34941-92-9) here.

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochems., and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. The authors present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using com. available silver(II) fluoride. The reactions occur at ambient temperature within 1 h with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Recommanded Product: 58081-05-3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Identification of Novel Glycosidic Aroma Precursors in Saffron (Crocus sativus L.). Author is Straubinger, Markus; Bau, Brigitte; Eckstein, Susanne; Fink, Margit; Winterhalter, Peter.

The methanolic extract of saffron was separated with the aid of multilayer coil countercurrent chromatog. After purification by HPLC, the following seven novel carotenoid metabolites were identified on the basis of their spectral (UV, FTIR, MS, NMR, CD) data: (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde O-β-D-gentiobioside (1), (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarboxylic acid O-β-D-glucopyranoside (2), 6-hydroxy-3-(hydroxymethyl)-2,4,4-trimethylcyclohexa-2,5-dienone 6-O-β-D-glucopyranoside (3), (2Z)-3-methylpent-2-enedioic acid 1-[1-(2,4,4-trimethyl-3,6-dioxocyclohexenyloxy)-O-β-D-glucopyranosid-6-yl] ester (4), (5S)-5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one O-β-D-glucopyranoside (5), (1R,5S,6R)-5-(hydroxymethyl)-4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one O-β-D-glucopyranoside (6), and (1R)- 3,5,5-trimethylcyclohex-3-enol O-β-D-glucopyranoside (7).

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Application In Synthesis of (R)-4-Hydroxydihydrofuran-2(3H)-one. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Taming carbohydrate complexity: a facile, high-yield route to chiral 2,3-dihydroxybutanoic acids and 4-hydroxytetrahydrofuran-2-ones with very high optical purity from pentose sugars. Author is Hollingsworth, Rawle I..

(S)-3,4-Dihydroxybutanoic acid and its γ-lactone [(S)-4-hydroxytetrahydrofuran-2-one] are important four-carbon synthons obtainable from some substituted D-hexose sugars and from L-malic acid. Until now there has been no easy route to the R-isomers because of the rarity both of suitably substituted L-hexose sugars and D-malic acid. Here we describe a method for preparing both enantiomeric forms of the free acids and their corresponding γ-lactones from pentose sugars.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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.Yin, Wei; Qiao, Chunhua researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Recommanded Product: 58081-05-3.They published the article 《Synthesis of Epigoitrin from (R)-(+)-4-Hydroxy-γ-butyrolactone》 about this compound( cas:58081-05-3 ) in Journal of Heterocyclic Chemistry. Keywords: epigoitrin preparation. We’ll tell you more about this compound (cas:58081-05-3).

Epigoitrin (I) is one of the major components of several natural species, including Isatis tinctoria (Isatis indigotica) Fort, Brassica rapa rapa (turnip) and Brassica oleracea capitata (cabbage). It presents antithyroid and antivirus activities. The synthesis of the target compounds was achieved using com. available (R)-(+)-4-hydroxy-γ-butyrolactone as a starting material.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one(SMILESS: O=C1OC[C@H](O)C1,cas:58081-05-3) is researched.SDS of cas: 86404-63-9. The article 《Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I》 in relation to this compound, is published in Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:58081-05-3).

A highly convergent asym. synthesis of the ansamycin antibiotics (+)-mycotrienin I (I) (R = cyclohexylcarbonyl-D-Ala) and (+)-mycotrienol (I) (R = H) (II) has been achieved through the synthesis and coupling of the C9-C16 subunit (III) and the aromatic subunit (IV). All four stereogenic centers were introduced using chiral allylsilane bond construction methodol. A key feature of the synthetic scheme includes the incorporation of the (E, E, E)-triene unit with simultaneous macrocyclization via a Stille-type coupling-macrocyclization.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Safety of 1,3-Diiodo-5,5-dimethylhydantoin. 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: 1,3-Diiodo-5,5-dimethylhydantoin, is researched, Molecular C5H6I2N2O2, CAS is 2232-12-4, about Hyperuricemia: risk factor for thromboembolism in hypertrophic cardiomyopathy patients.. Author is Wang, Ziqiong; Liao, Hang; Chen, Xiaoping; He, Sen.

Hyperuricemia has been regarded as a risk factor for various cardiovascular diseases. However, few studies have evaluated its influence on thromboembolism in hypertrophic cardiomyopathy (HCM) patients. The purpose of the present study is to investigate the association between hyperuricemia and thromboembolism in a retrospective HCM cohort. A total of 447 adult HCM patients were enrolled in this study from December 2008 to May 2016. Uric acid levels were measured at baseline. Hyperuricemia was defined as blood uric acid level > 360 µmol/L for female patients and > 420 µmol/L for male patients, respectively. The association between hyperuricemia and thromboembolism was analyzed. During the follow-up period of 1786.8 person-years, 31 patients (6.9%) developed thromboembolic events. There was a higher thromboembolism incidence in patients with hyperuricemia than those with normouricemia (8.9% vs. 5.6%; unadjusted HR 2.35, 95% CI 1.16-4.78, P = 0.018). The association slightly increased after adjusting for potential confounders (HR 2.67, 95% CI 1.24-5.76, P = 0.013). Atrial fibrillation (AF) and left ventricular outflow tract obstruction played an interactive role in the relationship between hyperuricemia and thromboembolism with P for interaction of 0.011 and 0.007, respectively. Adjusted HRs of hyperuricemia were 8.99 (95% CI 2.23-36.29, P = 0.002) for thromboembolism in HCM patients with AF and 6.89 (95% CI 2.23-21.24, P = 0.001) in non-obstructive HCM patients. The association lost statistical significance among patients without AF and obstructive ones. Hyperuricemia significantly predicts future thromboembolism in HCM patients, especially in HCM patients with AF and non-obstructive HCM patients. Future studies are warranted for further evaluation.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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, Phytochemistry called Aliphatic and aromatic glucosides from Anoectochilus koshunensis, Author is Ito, Aiko; Kasai, Ryoji; Yamasaki, Kazuo; Sugimoto, Hiroyuki, which mentions a compound: 58081-05-3, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3, Product Details of 58081-05-3.

A new simple aliphatic glucoside, 3-(R)-3-β-D-glucopyranosyloxybutanolide (kinsenoside) with its congeners and a heterocyclic aromatic glucoside, β-glucopyranosyl-3-pyridinemethanol (nicoloside) were isolated from whole plants of A. koshunensis. Their structures were elucidated from chem. and spectroscopic evidence.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Hollingsworth, Rawle I. published the article 《Taming carbohydrate complexity: a facile, high-yield route to chiral 2,3-dihydroxybutanoic acids and 4-hydroxytetrahydrofuran-2-ones with very high optical purity from pentose sugars》. Keywords: synthon hydroxybutanoic acid hydroxytetrahydrofuranone lactone preparation; hydroxybutanoic acid hydroxytetrahydrofuranone lactone preparation pentose sugar.They researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Quality Control of (R)-4-Hydroxydihydrofuran-2(3H)-one. 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:58081-05-3) here.

(S)-3,4-Dihydroxybutanoic acid and its γ-lactone [(S)-4-hydroxytetrahydrofuran-2-one] are important four-carbon synthons obtainable from some substituted D-hexose sugars and from L-malic acid. Until now there has been no easy route to the R-isomers because of the rarity both of suitably substituted L-hexose sugars and D-malic acid. Here we describe a method for preparing both enantiomeric forms of the free acids and their corresponding γ-lactones from pentose sugars.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Li, Meng; Wang, Dong-Hui published the article 《Copper-Catalyzed 3-Positional Amination of 2-Azulenols with O-Benzoylhydroxylamines》. Keywords: azulenol benzoylhydroxylamine copper catalyst regioselective amination; aminoazulenol preparation.They researched the compound: 4-Methoxypiperidine( cas:4045-24-3 ).Safety of 4-Methoxypiperidine. 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:4045-24-3) here.

A copper-catalyzed ortho-selective amination of 2-azulenols with O-benzoylhydroxylamines (RR’N-OBz) to synthesize ortho-aminoazulenols was reported. A wide range of functional groups on amines were compatible, furnishing the corresponding amino-azulene derivatives in moderate to good yields. The further synthetic elaboration using 3-amino-2-azulenols as starting materials was demonstrated.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Category: pyrrolines. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands. Author is Renk, Dana R.; Skraban, Marcel; Bier, Dirk; Schulze, Annette; Wabbals, Erika; Wedekind, Franziska; Neumaier, Felix; Neumaier, Bernd; Holschbach, Marcus.

With the aim to obtain potent adenosine A2A receptor (A2AR) ligands, a series of eighteen derivatives of 4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-1,3-benzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide were designed and synthesized. The target compounds were obtained by a chem. building block principle that involved reaction of the appropriate aminobenzothiazole Ph carbamates with either com. available or readily synthesized functionalized piperidines. Ki values for human A2AR ranged from 2.4 to 38 nM, with more than 120-fold selectivity over A1 receptors for all evaluated compounds except 4-Fluoro-4-(hydroxymethyl)-N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)piperidine-1-carboxamide which had a Ki of 361 nM and 18-fold selectivity. The most potent fluorine-containing derivatives exhibited Ki values of 4.9 nM, 3.6 nM and 2.8 nM for the human A2AR. Interestingly, the corresponding values for rat A2AR were found to be four to five times higher. Their binding to A2AR was further confirmed by radiolabeling with 18F and in vitro autoradiog. in rat brain slices, which showed almost exclusive striatal binding and complete displacement by the A2AR antagonist ZM 241385. Authors conclude that these compounds represent potential candidates for the visualization of the A2A receptor and open pathways to novel therapeutic treatments of neurodegenerative disorders or cancer.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem