Tag: M.W:100-200

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 Naphthyridine chemistry. V. One-step synthesis of 1,8-naphthyridines, published in 1967, which mentions a compound: 1569-17-1, Name is 4-Methyl-1,8-naphthyridine, Molecular C9H8N2, Electric Literature of C9H8N2.

cf. CA 66, 6881q; 65, 16955a; 64, 5057c. 2-Aminopyridine treated with Utermohlen’s “”sulfo-mix”” (CA 38, 9735) and glycerol gave 30% 1,8-naphthyridine. Similarly were prepared 2-methyl-, 4-methyl-, and 2,4-dimethyl-1,8-naphthyridines (I,II, and III). N.M.R. spectra data are given for the compounds

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

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).Application In Synthesis of Isoquinolin-5-amine hydrochloride. 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).

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

Recommanded Product: 4-Methyl-6-(methylthio)pyrimidin-2-ol. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol, is researched, Molecular C6H8N2OS, CAS is 16710-11-5, about 6-Substituted and 5,6-Disubstituted Derivatives of Uridine: Stereoselective Synthesis, Interaction with Uridine Phosphorylase, and in Vitro Antitumor Activity. Author is Felczak, Krzysztof; Drabikowska, Alicja; Vilpo, Juhani A.; Kulikowski, Tadeusz; Shugar, David.

Stereoselective procedures are described for the synthesis of 6-alkyluridines, e.g. I (R = F, OH, R1 = H, F), by Lewis acid-catalyzed condensation of trimethylsilylated 6-alkyl-4-alkylthiouracils with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) and trimethylsilylated 6-alkyl-3-benzyluracils with ABR. For all the foregoing nucleosides in the fixed syn conformation about the glycosyl bond, 1H NMR spectroscopy further demonstrated that the pentose rings exist predominantly in the conformation N (3′-endo). Most of the nucleosides were weak substrates of Escherichia coli pyrimidine nucleoside phosphorylase. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogs, 5-fluoro-6-(fluoromethyl)uridine and 5-fluoro-6-(hydroxymethyl)uridine, exhibited cytotoxicities comparable to that of 5-fluorouracil.

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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: 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, the main research direction is naphthyridine methylation MD calculation.Formula: C9H8N2.

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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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: 91523-50-1, is researched, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3Journal, Green Chemistry called A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion, Author is Ju, Shuyun; Qian, Mingxin; Li, Jing; Xu, Gang; Yang, Lirong; Wu, Jianping, the main research direction is enzymic redox cascade deracemization tetrahydroisoquinolinecarboxylate.COA of Formula: C10H11NO3.

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids are important chiral building blocks in the pharmaceutical and fine chem. industries. However, the existing chemo-enzymic deracemization method employing D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) suffers from the requirement for a large excess of a nonselective chem. reducing agent. To explore an alternative method, we envisaged a concurrent biocatalytic oxidation and reduction cascade in one pot. Herein, we report a novel biocatalytic route for the asym. reduction of 3,4-dihydroisoquinoline-1-carboxylic acids employing Δ1-piperidine-2-carboxylate/Δ1-pyrrolidine-2-carboxylate reductase from Pseudomonas putida KT2440 (PpDpkA) as a biocatalyst, yielding the corresponding (S)-1-carboxyl-substituted tetrahydroisoquinolines with high conversions and enantiomeric excess (>99% ee). By combining FsDAAO and PpDpkA in one pot, a fully biocatalytic method was demonstrated for the deracemization of a range of racemic 1-carboxyl substituted tetrahydroisoquinolines to produce the corresponding (S)-enantiomers with >99% conversions and >99% ee. Furthermore, preparative-scale biotransformation of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid gave the (S)-enantiomer with 89% isolated yield and >99% ee. Taken together, we provide an enantioselective biocatalytic redox cascade method for the one-pot synthesis of enantiopure 1,2,3,4-tetrahydroisoquinoline carboxylic acids.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – 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.Brown, Desmond J.; Shinozuka, Kazuo researched the compound: 4-Methyl-6-(methylthio)pyrimidin-2-ol( cas:16710-11-5 ).Product Details of 16710-11-5.They published the article 《Bis-s-triazolo[1,5-a:1′,5′-c]pyrimidine and some simple derivatives》 about this compound( cas:16710-11-5 ) in Australian Journal of Chemistry. Keywords: bistriazolopyrimidine; triazolopyrimidinamine acetoxyaminomethylene preparation cyclization. We’ll tell you more about this compound (cas:16710-11-5).

A general synthetic route to the new tricyclic system bis-s-triazolo[1,5-a:1′,5′-c]pyrimidine is reported. Thus the parent heterocycle (I; R = R1 = H) is prepared from the key bicyclic intermediate, s-triazolo[18k-c]pyrimidin-5-ylamine, through the 5-dimethylaminomethyleneamino, 5-hydroxyaminomethyleneamino and 5-acetoxyaminomethyleneamino derivatives, followed by final cyclization. I (R = H, Me, R1 = H, Me, Ph) are prepared similarly. Structures are confirmed by NMR spectra.

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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.Product Details of 1569-17-1.

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

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: 91523-50-1, is researched, Molecular C10H11NO3, about Synthesis and murine antineoplastic activity of bis[carbamoyloxymethyl] derivatives of pyrrolo[2,1-a]isoquinoline, the main research direction is pyrroloisoquinoline biscarbamoyloxymethyl; biscarbamoyloxymethylpyrroloisoquinoline preparation antineoplastic; cyclization glyoxylic acid hydroxyphenethylamino.Computed Properties of C10H11NO3.

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.

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Reference:
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: 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid(SMILESS: OC(=O)C1NCCC2=C1C=CC(O)=C2,cas:91523-50-1) is researched.Computed Properties of C7H5NO. The article 《Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase》 in relation to this compound, is published in Advanced Synthesis & Catalysis. Let’s take a look at the latest research on this compound (cas:91523-50-1).

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)-enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, resp.) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-ss-carbolines.

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1,8-Naphthyridine – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Naphthyridine chemistry. V. One-step synthesis of 1,8-naphthyridines》. Authors are Paudler, William W.; Kress, Thomas J..The article about the compound:4-Methyl-1,8-naphthyridinecas:1569-17-1,SMILESS:CC1=C2C=CC=NC2=NC=C1).SDS of cas: 1569-17-1. Through the article, more information about this compound (cas:1569-17-1) is conveyed.

cf. CA 66, 6881q; 65, 16955a; 64, 5057c. 2-Aminopyridine treated with Utermohlen’s “”sulfo-mix”” (CA 38, 9735) and glycerol gave 30% 1,8-naphthyridine. Similarly were prepared 2-methyl-, 4-methyl-, and 2,4-dimethyl-1,8-naphthyridines (I,II, and III). N.M.R. spectra data are given for the compounds

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1,8-Naphthyridine – Wikipedia,
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