Heterocyclic Building Blocks-Pyrrolines

Application In Synthesis of 4-Chloro-2-fluoropyridine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Chloro-2-fluoropyridine, is researched, Molecular C5H3ClFN, CAS is 34941-92-9, about Synthesis of N-alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives. Author is Hu, Gang; Xu, Jiaxi; Li, Pingfan.

N-Alkylated 2-pyridone products were obtained in good to excellent yields through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride activated sulfoxides and 2-fluoropyridine derivatives, followed by hydrolysis. This is a rare case that uses 2-fluoropyridine as a nucleophile in Pummerer type reactions.

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

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Chiral, biomimetic total synthesis of (-)-aplysistatin, published in 1982-11-05, which mentions a compound: 58081-05-3, mainly applied to aplysistatin Aplysia stereoselectivity total synthesis; cyclization biomimetic hydroxyhomogeranylbutyrolactone, Formula: C4H6O3.

The marine antineoplastic agent aplysistatin (I), from Aplysia angasi, was prepared enantiospecifically in 6 steps from R-(+)-malic acid. The key step was the biomimetic cyclization of lactone II with 2,4,4,6-tetrabromocyclohexa-2,5-dienone in MeNO2 at 20° for 2 h to give a 19:81 mixture of dihydroaplysistatins III (β-Br, β-Me, α-H; α-Br, α-Me, β-H).

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2,6-Dichloro-3-fluoropyridine, is researched, Molecular C5H2Cl2FN, CAS is 52208-50-1, about 2,6-Di(arylamino)-3-fluoropyridine Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors, the main research direction is diarylamino fluoropyridine preparation nonnucleoside reverse transcriptase inhibitor antiviral HIV.SDS of cas: 52208-50-1.

New non-nucleoside reverse transcriptase inhibitors (NNRTI), which are similar in structure to earlier described di(arylamino)pyrimidines but featuring a 2,6-di(arylamino)-3-fluoropyridine, 2,4-di(arylamino)-5-fluoropyrimidine, or 1,3-di(arylamino)-4-fluorobenzene moiety instead of a 2,4-disubstituted pyrimidine moiety, are reported. The short and practical synthesis of novel NNRTI relies on two sequential Pd-catalyzed aminations as the key steps. It is demonstrated through direct comparison with reference compounds that the presence of a fluorine atom increases the in vitro anti-HIV activity, both against the wild type virus and drug-resistant mutant strains. Three compounds, e.g., I, were found to display E50 close to 1.0 nM and a very high selectivity index (>40000).

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – 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: 4045-24-3, is researched, SMILESS is COC1CCNCC1, Molecular C6H13NOJournal, Article, ChemSusChem called Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature, Author is Cao, Yanwei; Huang, Yang; He, Lin, the main research direction is tertiary butoxycarbonyl amine preparation green chem; amine alc carbon monoxide tertiary butyloxycarbonylation gold copper catalyst; N-tert-butyloxycarbonylation; amines; gold catalysis; homogeneous catalysis; synergistic effect.Recommanded Product: 4-Methoxypiperidine.

Herein, a step- and atom-economic synthesis of N-Boc amines RC(O)OC(CH3)3 (R = diethylaminyl, piperidin-1-yl, 4-methylpiperazin-1-yl, 1,4-dioxa-8-azaspiro[4.5]decan-8-yl, etc.) from amines RH, t-butanol, and CO was reported at room temperature Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, com. available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implemented and, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcs. R1OH (R1 = t-Bu, 2-methylbutan-2-yl, Bn, etc.). Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

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

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Absolute stereochemistries of the aplysiatoxins and oscillatoxin A.COA of Formula: C4H6O3.

CD and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallog. anal. of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asym. carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochem. at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).

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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2,6-Dichloro-3-fluoropyridine(SMILESS: ClC1=NC(=CC=C1F)Cl,cas:52208-50-1) is researched.SDS of cas: 616-14-8. The article 《Synthesis of fluorinated pyridines by the Balz-Schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid》 in relation to this compound, is published in Journal of Heterocyclic Chemistry. Let’s take a look at the latest research on this compound (cas:52208-50-1).

Fluorination of the 2,6-disubstituted 3-aminopyridines I (R = SEt, pyrrolidino, 4-ethoxycarbonylpiperazino, 4-acetylpiperazino, R1 = NHAc; R = R1 = Cl) by the Balz-Schiemann reaction gave 3-pyridinediazonium tetrafluoroborates which were heated with or without a solvent to give the corresponding fluorinated pyridines, in good yields. 2-Substituted 6-acetylamino-3-fluoropyridines were converted by a known method into a series of 7-substituted 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids including enoxacin (II).

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

Formula: C5H3ClFN. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Chloro-2-fluoropyridine, is researched, Molecular C5H3ClFN, CAS is 34941-92-9, about The reactivity of 2-fluoro- and 2-chloropyridines toward sodium ethoxide: Factors governing the rates of nucleophilic (het)aromatic substitutions. Author is Schlosser, Manfred; Rausis, Thierry.

The relative displacement rates of the halide substituent from 2-fluoro- and 2-chloropyridines by EtONa in EtOH at +25° were assessed by competition kinetics. The 2-fluoropyridine reacts 320 times faster than the chloro analog. A CF3 group increases the reactivity more than single halogen atoms do, whatever the element, and the latter are superior to Me3Si groups. Substituents accommodated at the 4-position operate through their inductive effect, whereas at the 3-position, this action may be attenuated by steric hindrance. Almost all 5-substituents enhance the rate of the nucleophilic substitution occurring at the 2-position. The sole exception concerns the F-atom at the 5-position which retards the reaction, presumably by lone-pair/lone-pair repulsion with the neg. charge building up at the central C-atom of the intermediate Meisenheimer complex. The substituent effects are additive. Therefore, by using the increments derived from the present work, the rates of future reactions should be predictable with fair accuracy.

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

Li, Xuemei; Hong, Duidui; Zhang, Mengmeng; Xu, Lei; Zhou, Yubo; Li, Jia; Liu, Tao published the article 《Development of peptide epoxyketones as selective immunoproteasome inhibitors》. Keywords: epoxyketone peptide synthesis peptidomimetic immunoproteasome inhibitor structure activity; antitumor agent drug design mol docking hydrogen bond chirality; isocyanate peptide coupling; Epoxyketones; Immunoproteasome inhibitor; Multiple myeloma; Selectivity.They researched the compound: 4-Methoxypiperidine( cas:4045-24-3 ).Product Details of 4045-24-3. 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 series of epoxyketone analogs with varying N-caps and P3-configurations were designed, synthesized and evaluated. We found that D-Ala in P3 was crucial for β5i selectivity over β5c. Notably, compounds (I) (R1 = II) (β5i IC50 = 26.0 nM, 25-fold selectivity) and I (r1 = III) (β5i IC50 = 25.1 nM, 24-fold selectivity) with the D-configuration at P3 were the most selective inhibitors. Although I (R1 = II and III) showed only moderate anti-proliferative activity against RPMI-8226 and MM.1S cell lines, based on our experiments, it indicates that the inhibition of β5i alone is not sufficient to exert anticancer effects and may rely on the complementary inhibition of β1i, β5c and β5i. These data further increase our understanding of immunoproteasome inhibitors in hematol. malignancies.

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

Schrader, Thomas O.; Zhu, Xiuwen; Kasem, Michelle; Li, Sufang; Liu, Chunyan; Ren, Albert; Wu, Chunrui; Semple, Graeme published the article 《Asymmetric syntheses of (R)-4-halo-6,6a,7,8,9,10-hexahydro-5H-pyrazino[1,2-a][1,n]naphthyridines, important 5-HT2C agonist precursors》. Keywords: halo pyrazinonaphthyridine diastereoselective synthesis precursor 5HT2C agonist.They researched the compound: 4-Chloro-2-fluoropyridine( cas:34941-92-9 ).Related Products of 34941-92-9. 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.

Asym. syntheses of N-protected (R)-4-halo-6,6a,7,8,9,10-hexahydro-5H-pyrazino[1,2-a][1,n]naphthyridines, advanced intermediates for the synthesis of highly potent and selective 5-HT2C agonists, are described. The key transformation involves ring opening of N-protected bicyclic sulfamidate (R)-hexahydro-3H-pyrazino[1,2-c][1,2,3]oxathiazine 1,1-dioxide with (4-halo-2-fluoropyridin-3-yl)lithiums or (3-bromo-5-fluoropyridin-4-yl)lithium. In situ hydrolyzes of the resultant sulfamic acids and subsequent intramol. nucleophilic aromatic substitutions (SNAr) produce the enantiopure tricycles. The two step procedure represents new methodol. for the stereoselective syntheses of tetrahydronaphthyridines.

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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, European Journal of Organic Chemistry called Inversion of configuration of (S)-β-hydroxy-γ-butyrolactone with total retention of the enantiomeric purity, Author is De Angelis, Francesco; De Fusco, Enrico; Desiderio, Paola; Giannessi, Fabio; Piccirilli, Fabrizio; Tinti, Maria Ornella, which mentions a compound: 58081-05-3, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3, Product Details of 58081-05-3.

The inversion of configuration of (S)-β-hydroxy-γ-butyrolactone to its (R) enantiomer is reported with total retention of the enantiomeric purity by a 4-step procedure. The (R) enantiomer was thus synthesized with an overall chem. yield of 47% and >97% ee. This transformation opens an economic route to the production of (R)-GABOB and (R)-carnitine, among other biol. active compounds, from a D-hexose source, or, alternatively, from the industrial waste compound (S)-carnitine. During the reaction sequence, the intermediate (R)-β-(hydroxymethyl)-β-propiolactone is also prepared, which is now under investigation as a chiral synthon for new synthetic applications.

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