Month: March 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of iodo derivatives of the furan series. 5-Iodofurfural》. Authors are Nazarova, Z. N..The article about the compound:5-Iodo-2-furaldehydecas:2689-65-8,SMILESS:IC1=CC=C(O1)C=O).Synthetic Route of C5H3IO2. Through the article, more information about this compound (cas:2689-65-8) is conveyed.

All 5-bromo or -iodo derivatives of furan lose halogen quant. on standing 48 h. in the dark in HNO3 (d. 1.4) in the presence of AgNO3, followed by heating to 50-60° until N oxide vapor appear; the method can be used for anal. of these compounds Refluxing 35 g. 5-bromofurfural with 3.5 g. KI and 180 mL. AcOH 1 h., followed by dilution with H2O gave 96% crude product, m. 124-6°, which gave 80% pure 5-iodofurfural, m. 127.5-8° (from EtOH); with HNO3 it gives vapor of iodine; oxime, decompose 167-8°; semicarbazone, decompose 199-200°. The aldehyde in 30% NaOH treated with a few drops H2O2 and kept 4 days, then acidified, gave 58.8% 5-iodofurancarboxylic acid, decompose 197-8° (from H2O). The aldehyde heated with Ac2O-AcOK at 145-50°, then boiled with a little H2O 15 min. gave 82.2% 5-iodo-2-furylacrylic acid, decompose 159-60° (from dilute dioxane). The aldehyde condensed with MeNO2 (cf. C.A. 49, 9606b) gave 86% 1-(5-iodo-2-furyl)-2-nitroethylene (I), yellow-orange, m. 112-13° (from EtOH); if the intermediately formed Na salt is filtered directly from the mixture and is carefully decomposed with AcOH after washing with Et2O and MeOH, there is formed the unstable nitro alc., orange-red oil, which after steam distillation gave 80% I, m. 112-13°. The Br analog heated with KI and NaI in AcOH 2 h. on a steam bath gave 82.6% I. Heating 2-(5-bromo-2-furyl)-1-chloro-1-nitroethylene (cf. loc. cit.) with NaI in AcOH 2 h. gave 48.2% 5-iode analog, C6H3BrCINO3, m. 109-9.5° (from EtOH), an irritant which loses iodine on heating with HNO3.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Iodo-2-furaldehyde(SMILESS: IC1=CC=C(O1)C=O,cas:2689-65-8) is researched.Name: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. The article 《Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation》 in relation to this compound, is published in Science (Washington, DC, United States). Let’s take a look at the latest research on this compound (cas:2689-65-8).

The enzymic β-C-H hydroxylation of the feedstock chem. isobutyric acid has enabled the asym. synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective β-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched α-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous iso-Pr moieties by organometallic catalysts has remained an unanswered challenge. Herein, the authors report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of iso-Pr groups via palladium insertion into the C(sp3)-H bonds of one of the prochiral Me groups. We detail the enantioselective β-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of α-chiral centers.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – 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: 2689-65-8, is researched, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2Journal, Revista sobre los Derivados de la Cana de Azucar called Preparation and properties of 3,5-disubstituted rhodanines, Author is Torres, D.; Reig, R., the main research direction is rhodanine benzylfurfurylidene; benzylrhodanine furfurylidene; furfurylidenerhodanine benzyl.Application In Synthesis of 5-Iodo-2-furaldehyde.

3-Benzyl-5-furfurylidenerhodanines I (R = H, Cl, Br, I) were prepared by condensation of 3-benzylrhodanine (II) with furfural or its 5-halo derivatives in AcOH-AcONa. II was prepared by treatment of PhCH2NH2 with CS2 and KOH, condensation of the resulting PhCH2NHCS2K with ClCH2CO2K, and cyclization in the presence of concentrated HCl.

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1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

SDS of cas: 2689-65-8. 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. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Stereospecific Synthesis of Tri- and Tetrasubstituted α-Fluoroacrylates by Mizoroki-Heck Reaction.

Ligand-free, efficient, palladium-catalyzed Mizoroki-Heck reaction between Me α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quant. yields of fluoroalkenes. The Mizoroki-Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki-Heck reaction, allows the synthesis of fluorinated analogs of therapeutic agents with high yield.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

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 Functionalization of C(sp3)-H bonds using a transient directing group, published in 2016-01-15, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, Electric Literature of C5H3IO2.

Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the β or γ positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Study of copper, nickel, and zinc electroplating in the presence of some furaldehydes, the main research direction is copper electroplating furaldehyde structure; zinc electroplating furaldehyde structure; nickel electroplating furaldehyde structure; substituent constant furaldehyde electroplating.Application of 2689-65-8.

On the basis of the linearity principle of free energies, a quant. evaluation was made of the effect of the structure of furfural derivatives (I; R = H, Cl, I, Br, CHO, Ph, Me, OMe, Et2N, Me2N) on the kinetics of electroplating of Cu, Ni, and Zn. A correlation was established between electrochem., adsorption,and spectral characteristics of the studied furaldehydes and the substituent constants of their mols.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – 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: 2689-65-8, is researched, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2Journal, Article, Research Support, Non-U.S. Gov’t, Organic Letters called Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides, Author is Chen, Bing-Zhi; Zhi, Man-Ling; Wang, Chuang-Xin; Chu, Xue-Qiang; Shen, Zhi-Liang; Loh, Teck-Peng, the main research direction is alkyl chloride substrate alkylindium reagent; palladium catalyzed cross coupling aryl halide alkylindium.COA of Formula: C5H3IO2.

An efficient method for the preparation of alkyl indium reagents by using unactivated and cheap alkyl chlorides as substrates in the presence of indium and LiI was developed. The thus-formed alkyl indium species effectively underwent palladium-catalyzed cross-coupling reactions with aryl halides with wide functional group tolerance.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – 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: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Naphthyridine chemistry. VIII. Mass spectra of the 1,x-naphthyridines and some of their methyl derivatives.Reference of 4-Methyl-1,8-naphthyridine.

The mass spectra of the four parent 1,x-naphthyridines, the 2-, 3-, and 4-monomethyl-1,5-, 1,6-, and 1,8-naphthyridines, seven dimethyl-1,8-naphthyridines, and one trimethyl-1,8-naphthyridine are reported. Evidence for an azatropylium ion intermediate in the fragmentation of the methyl compounds is presented. The fragmentation modes of the naphthyridines are similar to those for the quinolines in addition to several new processes.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Reference of 4-Methyl-1,8-naphthyridine. 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: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Syntheses of nitrogen-containing compounds. XVII. Improvement of one-step synthesis of naphthyridine derivatives and their methylation with demethyl sulfoxide in the presence of base. Author is Hamada, Yoshiki; Takeuchi, Isao; Hirota, Minoru.

1,8-Naphthyridines were synthesized in a high yield by the reaction of 2-aminopyridines with glycerol, in the presence of Na m-nitrobenzenesulfonate, in H2SO4. Methylation of naphthyridines with Me2SO in the presence of NaH or KOBu-tert afforded their mono-Me or di-Me compounds This methylation with methylsulfinyl carbanion was examined from the Hueckel MO method; the calculation agreed with the exptl. results.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – 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, Yakugaku Zasshi called Nitration of isoquinoline 2-oxide, Author is Ochiai, Eiji; Ikehara, Morio, which mentions a compound: 152814-23-8, SMILESS is NC1=CC=CC2=C1C=CN=C2.[H]Cl, Molecular C9H9ClN2, SDS of cas: 152814-23-8.

Isoquinoline 2-oxide (I) (5 g.) in 20 g. concentrated H2SO4 and 5 g. KNO3, heated 3 hrs. at 60°, the mixture poured into ice water, made alk. with Na2CO3, and the product recrystallized from Me2CO give 4.5 g. 5-nitroisoquinoline 2-oxide (II), yellow needles, m. 220°. Chromatographic separation of the mother liquor in C6H6 gives 0.1 g. C9H6O3N2 (III), m. 179-80°. III (0.1 g.) in 10 ml. CHCl3 heated 10 min. at 50° with 1 ml. PCl3, let stand 3 hrs., the product poured into ice water, and the mixture made alk. with Na2CO3 and extracted with CHCl3 gives 0.1 g. C9H6O2N2 (IV), needles, m. 70°; catalytic reduction of 70 mg. IV in 10 ml. alc. with Pd-C (1 ml. 1% PdCl2 and 0.2 g. C) gives 70 mg. sirupy product (IVA), which, diazotized in 2 ml. 15% HCl at 0-2° with 20 mg. NaNO2 in 0.5 ml. water, and the solution poured into Cu2Cl2 (0.2 g. CuCl2, 1 ml. water, 0.5 ml. concentrated HCl, and 0.1 g. Zn), made alk. with Na2CO3, and extracted with Et2O, gives 8-chloroisoquinoline (V), needles, m. 55°; picrate, m. 190°. Catalytic reduction of 0.5 g. II in 40 ml. alc. with 0.2 g. Pd-C (60%), 10 ml. 10% HCl, and H gives 0.3 g. 5-aminoisoquinoline (VI), needles, m. 124-5°; picrate, m. 226-8°; VI.HCl, m. 270° (decomposition); VI acetate, m. 145-6°. The mother liquor from VI in C6H6 passed through Al2O3 gives a small amount of 5-amino-1,2,3,4-tetrahydroisoquinoline (VII), prisms, m. 150-1°; HCl salt, m. 308-9°, picrate, m. 205-6° (decomposition). VII (50 mg.) in 1 ml. Ac2O and a small amount of AcONa heated 2 hrs. at 100°, the Ac2O removed in vacuo, and the residue made alk. with Na2CO3 and extracted with Et2O gives 40 mg. 5-acetamido-2-acetyl-1,2,3,4-tetrahydroisoquinoline, needles, m. 155-6° (from C6H6). Catalytic reduction of 0.5 g. II in 40 ml. alc. with 0.2 g. Pd-C (60%) and H 70 min. gives 0.4 g. VI and 0.1 g. 5-aminoisoquinoline 2-oxide (VIII), needles, m. 225°. VIII (0.1 g.) in 10 ml. CHCl3 and 1 ml. PCl3 refluxed 30 min. on a water bath, and the mixture cooled, made alk. with Na2CO3, and extracted with CHCl3 gives 70 mg. VI. VI (0.2 g.) in 5 ml. 20% NaHSO3 heated 6 hrs. at 150° in a sealed tube, the product made alk. with NaOH, extracted with C6H6, the aqueous layer acidified with HCl, evaporated to dryness, the residue taken up with a small amount of water, the solution saturated with Na2CO3, and the precipitate recrystallized from alc. gives 0.1 g. 5-hydroxyisoquinoline, prisms, m. 230° (decomposition).

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem