Month: April 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nitration of isoquinoline 2-oxide》. Authors are Ochiai, Eiji; Ikehara, Morio.The article about the compound:Isoquinolin-5-amine hydrochloridecas:152814-23-8,SMILESS:NC1=CC=CC2=C1C=CN=C2.[H]Cl).Electric Literature of C9H9ClN2. Through the article, more information about this compound (cas:152814-23-8) is conveyed.

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).

There are many compounds similar to this compound(152814-23-8)Electric Literature of C9H9ClN2. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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, Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya called Study of copper, nickel, and zinc electroplating in the presence of some furaldehydes, Author is Kuznetsov, V. V.; Grigor’ev, V. P.; Fadeeva, O. V.; Nazarova, Z. N., which mentions a compound: 2689-65-8, SMILESS is IC1=CC=C(O1)C=O, Molecular C5H3IO2, Quality Control of 5-Iodo-2-furaldehyde.

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.

There are many compounds similar to this compound(2689-65-8)Quality Control of 5-Iodo-2-furaldehyde. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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 A simple preparative synthesis of epoxy[1,3]oxazino(or oxazolo)[2,3-a]isoindoles and their thia analogues via IMDAF, the main research direction is epoxy oxathiazino isoindole carboxylic acid preparation; intramol Diels Alder cycloaddition furfural amino alc.Recommanded Product: 5-Iodo-2-furaldehyde.

Azomethines, easily prepared from 5-(R)-furfurals and 1,3- or 1,2-amino alcs. (aminothiols), react under mild conditions with maleic anhydride affording 8,10a-epoxy[1,3]oxa(thia)zino[2,3-a]isoindole-7- and 7,9a-epoxy[1,3]oxa(thia)zolo[2,3-a]isoindole-6-carboxylic acids. The reaction proceeds through initial N-acylation with subsequent intramol. exo-Diels-Alder cycloaddition and stereoselectively leads to the exo adducts. The ‘one-pot’ synthetic protocol is also presented.

There are many compounds similar to this compound(2689-65-8)Recommanded Product: 5-Iodo-2-furaldehyde. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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, Collection of Czechoslovak Chemical Communications called Furan derivatives. LV. Kinetics of condensation of 5-nitrofurfuryl sulfones with aldehydes, Author is Knoppova, V.; Jurasek, A.; Kovac, J.; Guttmann, M., the main research direction is kinetics condensation aldehyde nitrofurfuryl sulfone; substituent effect condensation aldehyde nitrofurfuryl sulfone; reaction constant condensation aldehyde nitrofurfuryl sulfone; furfuryl sulfone condensation aldehyde nitrofurfuryl sulfone.COA of Formula: C5H3IO2.

The kinetics of the condensation of I with II (R = H, Me, iodo, Cl, Br, CO2Me NO2) or III (R = H, NO2, Cl, Br, CO2H, CO2Et, Me, MeO, NHAc) [to give, resp., the corresponding (E)-IV or (E)-V, examined in NH4OAc-piperidine at 118° or MeOH-piperidine at 40°, were 2nd order. The log k was linearly related with σp+. The pKa of I and of 5-nitrofurfuryl Me sulfone (VI) were determined and the rates of the condensation of I or VI with III (R = NO2) indicated that steric factors were more important in the condensation than was the sulfone acidity.

There are many compounds similar to this compound(2689-65-8)COA of Formula: C5H3IO2. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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: 5-Iodo-2-furaldehyde, is researched, Molecular C5H3IO2, CAS is 2689-65-8, about Derivatives of the ethyl ester of (α-cyanofurylacrylic acid)..Product Details of 2689-65-8.

Derivatives of Et α-cyanofurylacrylate (I; R = H, NO2, Br, I) were synthesized and tested for fungicidal activity. In vitro against 9 fungi, I (R = NO2) gave >90% inhibition of 5 species (Penicillium italicum, P. digitatum, Phytophthora nicotianae, Helminthosporium oryzae, and Phomopsis citri). As a 0.3% spray, it gave good control of blue mold of tobacco in pot experiments

There are many compounds similar to this compound(2689-65-8)Product Details of 2689-65-8. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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

HPLC of Formula: 91523-50-1. 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: 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, is researched, Molecular C10H11NO3, CAS is 91523-50-1, about Synthesis and murine antineoplastic activity of bis[carbamoyloxymethyl] derivatives of pyrrolo[2,1-a]isoquinoline.

The title compounds I (R = Me2CH, cyclohexyl, R1 = MeO; R = Me, Et, cyclohexyl, R1 = H) were prepared I (R1 = MeO) were prepared from m-(PhCH2O)C6H4CHO via phenolic cyclization of m-HOC6H4CH2CH2NH2 with glyoxylic acid to give the isoquinoline II, which underwent cyclization with MeO2CCCCO2Me to give the pyrroloisoquinoline III. All I had P 388 lymphocytic activity. I (R = Me2CH, R1 = MeO) was tested in an expanded tumor panel and was shown to be active against B16 melanocarcinoma, CD8F1 mammary, L1210 lymphoid leukemia, colon 38, and MX-1 human tumor breast xenograft systems.

There are many compounds similar to this compound(91523-50-1)HPLC of Formula: 91523-50-1. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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

Kaigorodova, E.A.; Kvak, S. N.; Ugrak, B. I.; Zaplishnyi, V. N.; Kul’nevich, V. G. published the article 《Studies on furopyridines. VI. Synthesis and stereostructure of hetarylmethylene-3-oxo-4-thiofuro[3,4-c]pyridines》. Keywords: furopyridine thio hetarylmethylene preparation stereochem; regioselective condensation heteroaromatic aldehyde thiofuropyridine.They researched the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ).COA of Formula: C5H3IO2. 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:2689-65-8) here.

Condensation reaction of 6-methyl-3-oxo-4-thio-1H-furo[3,4-c]pyridine with heteroaromatic aldehydes proceeds regioselectively at the methylene center to give Z isomers of title compounds I (R = H, Z = O, S; R = Me, Br, iodo, Z = O) in s-cis conformations for furfuryl and in s-trans conformations for thenylmethylene derivatives

There are many compounds similar to this compound(2689-65-8)COA of Formula: C5H3IO2. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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 Preparation of Aryl and heteroaryl indium(III) reagents by the direct insertion of indium in the presence of LiCl, published in 2008, which mentions a compound: 2689-65-8, Name is 5-Iodo-2-furaldehyde, Molecular C5H3IO2, Application of 2689-65-8.

Sensitive functional groups, including ketone, aldehyde, and ester groups, may be present in aryl In reagents prepared in good to excellent yields by the treatment of aryl and heteroaryl iodides with In powder in the presence of LiCl. These functionalized organoindium(III) reagents readily undergo Pd-catalyzed cross-coupling with functionalized aryl iodides, including those containing NH or OH groups.

There are many compounds similar to this compound(2689-65-8)Application of 2689-65-8. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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

Electric Literature of C9H8N2. 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: 4-Methyl-1,8-naphthyridine, is researched, Molecular C9H8N2, CAS is 1569-17-1, about Nuclear magnetic resonance studies on σ-adducts of heterocyclic systems with nucleophiles. 18. Proton and carbon-13 nuclear magnetic resonance investigations on σ-adduct formation between 1,X-naphthyridines and some methyl-1,8-naphthyridines with potassium amide in liquid ammonia. Author is Van der Plas, H. C.; Van Veldhuizen, A.; Wozniak, M.; Smit, P..

The 1,5-, 1,6-, and 1,8-naphthyridines dissolved in liquid NH3 containing KNH2 showed the H-2 and C-2 resonance at about 4 and 90 ppm higher field, resp., than the H-2 and C-2 resonance of the naphthyridines observed in CDCl3 as NH2- added to all 3 naphthyridines at C-2 to give a 2-amino-1,2-dihydro-1,X-naphthyridinide ion. The 1,7-naphthyridine showed a more complex reactivity pattern toward NH2-. Besides addition at C-2, addition at C-6 and at C-8 is observed The relation of this study with that of the Chichibabin amination of the 1,X-naphthyridines is discussed. NH2- and 2-methyl- and 4-methyl-1,8-naphthyridine gave only deprotonation of the Me group; 3-methyl-1,8-naphthyridine and NH2- gave the 2-amino-1,2-dihydro-3-methyl-1,8-naphthyridinide ion.

There are many compounds similar to this compound(1569-17-1)Electric Literature of C9H8N2. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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, Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen called Synthesis of 1,8-naphthyridine homologs and their hydrogenation, Author is Ochiai, Eiji; Miyaki, Komei, which mentions a compound: 1569-17-1, SMILESS is CC1=C2C=CC=NC2=NC=C1, Molecular C9H8N2, COA of Formula: C9H8N2.

In earlier work (CA 33:2525.5) it was found that Me 1,4-dihydroxy-2,5-naphthyridine-3-carboxylate (C. A. numbering, 5,8-dihydroxy-1,6-naphthyridine-7-carboxylate) and the 1-Cl compound on catalytic hydrogenation take up H only on the nonsubstituted pyridine ring. In continuation of this work, 2,4-dimethyl- (I) and 4-methyl-1,8-naphthyridine (II) have been synthesized and a similar phenomenon on hydrogenation has been observed. In the meantime some other 1,8-naphthyridines described in this paper have been prepared by analogous methods by Mangini (preceding abstract). 7-Amino derivative of I (0.5 g. from 2 g. 2,6-diaminopyridine, 2 g. CH2Ac2 and 1 g. fused ZnCl2 heated 3 hrs. at 120-30°), m. 220° (Ac derivative, pale yellow, m. 300°), converted by diazotization in 40% H2SO4 into the 7-HO compound, m. 251°, which, heated 30 min. in a sealed tube at 140° with POCl3, gives the 7-Cl compound, m. 146-7°; this, boiled 30 min. with 20% MeONa in MeOH, gives the 7-MeO compound, m. 65° (picrate, m. 188-9°). Hydrogenation of 1 g. of the HO compound in 20 g. alc. with 1 g. Ni-kieselguhr under 110 atm. of H for 10 hrs. at 170-80° gave, along with 0.6 g. unchanged material, 0.2 g. of a dihydro derivative, C10H12N2O, m. 175-80°. The Cl compound (0.5 g.), shaken in 10% KOH-MeOH with 0.2 g. of 20% Pd-charcoal and H until about 1.2 mols. H had been absorbed, and the product chromatographed in benzene through Al2O3, yielded about 0.05 g. I, m. 85-6° (HCl salt, decomposes 240°; picrate, decomposes 204-6°; methiodide, yellow needles with 1 H2O, m. 93-4; chloroplatinate, I.H2PtCl6, decomposes 242-4°; chloroaurate, decomposes 166-7°). When 0.1 g. of the Cl compound in 10 cc. of 10% KOH-MeOH was hydrogenated to saturation with 0.5 g. of 20% Pd-charcoal it yielded the tetrahydro derivative (III) of I described below. With 1.2 g. of the Cl compound in 20 cc. of 5% KOH-MeOH, 0.5 g. PdO-CaCO3 and a trace of Pd-charcoal, the hydrogenation stopped in 30 min. (about 170 cc. H absorbed) and 0.8 g. I was obtained. Shaken in 10 cc. AcOH with 0.1 g. Pt oxide and H to saturation, 0.5 g. I absorbed about 160 cc. H and yielded 0.5 g. of a tetrahydro derivative (III), m. 118°, giving a pos. Liebermann reaction (picrate, m. 207°; Ac derivative, m. 42-3°); III was also obtained in 0.85-g. yield from 1 g. I in 50 cc. cyclohexane and 5 cc. alc. with 1 g. Raney Ni heated under an initial H pressure of 70 atm. 2 hrs. at 120° and 2 hrs. at 190°. III was unchanged by 4 hrs. treatment in AcOH with Pt oxide and 110 atm. H pressure, at room temperature With Na in boiling alc., however, it yielded the decahydro derivative of I, easily subliming needles, m. 92-3° (di-Ac derivative, thick oil, b0.02 135-45°). 2,7-Dichloro-4-methyl-1,8-naphthyridine in 10% KOH-MeOH hydrogenated with PdO-CaCO3 and a trace of Pd-charcoal gave, together with a mono-Cl compound, C9H7ClN2, m. 104°, chiefly (about 70%) II, b0.05 147-8° (picrate, decomposes 204-5°; perchlorate, m. 180-1°). II (1 g.) in 10 cc. AcOH with 0.5 g. Pt oxide and H yielded a mixture of 2 isomeric tetrahydro derivatives, separated by fractional crystallization from petr. ether: 0.2 g. of a more soluble isomer A (IV), m. 62-3°, giving a pos. Liebermann reaction (Bz derivative, m. 86-7°), and about 0.8 g. of a less soluble isomer B (V), m. 102-3° (picrate, decomposes 248°; Bz derivative, m. 105-6°; nitro derivative, m. 217-18° and giving a pos. Liebermann reaction, prepared by treating the tetrahydride in cold H2SO4 (dry ice-acetone) with fuming HNO3 (d.1.6), pouring on ice, crystallizing from alc., heating the crystals (m. 124-5°) in concentrated H2SO4 at 60°, again pouring on ice, filtering, making alk. with Na2HPO4 and extracting with ether). V is unchanged by hydrogenation in AcOH with PtO and 65 atm. H pressure. With Na in boiling AmOH, both isomers yield the same (racemic) decahydro derivative of II, b0.1 70-80°, m. 87°, gives a pos. Liebermann reaction (picrate, decomposes 210°). The structures of III, IV and V have not been definitely established but the following considerations make it highly probable what they are. The work of earlier investigators on the hydrogenation of quinoline homologs with Ni and H under pressure and with Sn and HCl has shown that Me groups have a disturbing influence on the hydrogenation of the ring half on which they are substituted whereas Na and alc. readily hydrogenate the Me-substituted rings. This disturbing effect of Me groups is ascribed to the inductive effect of the Me group. III is considered to be the 5,6,7,8-tetrahydro compound To further confirm this, III was heated in a little alc. with an excess of ClCH2COMe for 4 hrs. at 100°; the resulting addition product, C15H21ClN22O2, m. 181-2°, allowed to stand 1 day in a little water with 2 drops of 10% Na3CO3, gave, in addition to unchanged III, a resin whose blue Ehrlich reaction pointed to the presence of an indolizine ring. Such a ring can be formed only from a nonhydrogenated 2-methylpyridine. IV is considered to be the 1,2,3,4- and V the 5,6,7,8-tetrahydro compound because the latter is formed in the larger amount; its higher m. p. is also in harmony with such an assumption.

There are many compounds similar to this compound(1569-17-1)COA of Formula: C9H8N2. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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