Tag: M.W=100-200

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-(4-Pyridyl)-1H-tetrazole(SMILESS: C1(C2=NN=NN2)=CC=NC=C1,cas:14389-12-9) is researched.Quality Control of 5-(4-Pyridyl)-1H-tetrazole. The article 《Syntheses of 5-Substituted 1H-Tetrazoles Catalyzed by Reusable CoY Zeolite》 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:14389-12-9).

A simple and efficient route for the synthesis of 5-substituted 1H-tetrazoles catalyzed by CoY zeolite is reported. The salient features of this atom-economical, cost-effective, and high-yield cobalt-catalyzed protocol are aerobic conditions, lower reaction time, and milder reaction conditions without additives. Other advantages include exptl. ease of manipulation, safer alternative to hazardous, corrosive, and polluting conventional Lewis acid catalysts, recovery, and reusability with consistent catalytic activity. The results are rationalized by proposing a suitable mechanism.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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 Effect of substrate analogs on the circular dichroic spectra of thymidylate synthetase from Lactobacillus casei, published in 1975, which mentions a compound: 20198-19-0, Name is 2-Aminoquinazolin-4(3H)-one, Molecular C8H7N3O, Formula: C8H7N3O.

CD studies at 290-400 nm with thymidylate synthetase from L. casei revealed characteristic Cotton effects in the presence of various folate analogs plus 5-fluoro-2′-deoxyuridylate (I). Omission of either substrate analog prevented the appearance of the Cotton effects. When I and racemic 5,10-methylenetetrahydrofolate (II) were mixed with the enzyme, a ternary complex resulted which gave distinctive minor neg. ellipticity bands at 285 and 332 nm and a major pos. band at 305 nm. Similar results were obtained with the ternary complex containing (+)-II but the enzymically inactive (-)-II induced only the pos. band at 305 nm. More intense Cotton effects were elicited by (±)-5,11-methylenetetrahydrohomofolate with a major pos. ellipticity band at 308 nm and a minor neg. band at 335 nm. A ternary complex was also formed with dihydrofolate, which provided a major CD band at 305 nm and a broad minor neg. band in the region of 335 nm. Deoxyuridylate and thymidylate also formed ternary complexes with dihydrofolate, but their ellipticity bands were much less intense. Other folate analogs that formed ternary complexes with I to provide characteristic CD spectra were tetrahydrofolate, tetrahydrohomofolate, 10-methyltetrahydrofolate, and 2-amino-4-hydroxyquinazoline. By measuring the increment in ellipticity at 305 nm on addition of specific ligands to enzyme solutions, it was determined that the L. casei thymidylate synthetase contains 2 binding sites for I and for each of the diastereoisomers of II. An improved procedure is presented for the large-scale purification and crystallization of L. casei thymidylate synthetase.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about Monodisperse Pt NPs@rGO as highly efficient and reusable heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazole derivatives.Reference of 5-(4-Pyridyl)-1H-tetrazole.

Monodisperse platinum nanoparticles supported on reduced graphene oxide (Pt NPs@rGO) are stable, isolable, bottleable, long-lived, highly efficient and exceptionally reusable heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles e. g., I, from sodium azide and various aromatic nitriles with great catalytic performance. Pt NPs@rGO have been used for the first time for these types of synthesis reactions and these NPs were characterized by transmission electron microscopy (TEM), high resolution electron microscopy (HRTEM), X-ray diffraction (XRD), at. force microscopy (AFM) and XPS. All prepared tetrazole compounds were obtained with the highest yield by using the current heterogeneous catalyst and characterized by m.p., FT-IR, 1H-NMR, 13C-NMR and HRMS analyses.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Aureggi, Valentina; Sedelmeier, Gottfried published the article 《1,3-Dipolar cycloaddition: click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles》. Keywords: substituted tetrazole preparation; organoaluminum azide preparation nitrile dipolar cycloaddition.They researched the compound: 5-(4-Pyridyl)-1H-tetrazole( cas:14389-12-9 ).Electric Literature of C6H5N5. 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:14389-12-9) here.

Conventional methods to prepare tetrazoles employ dangerous, toxic reagents. A route to these heterocycles using inexpensive and nontoxic dialkyl aluminum azides was developed. The cycloaddition occurred under mild conditions and tolerates a variety of functional groups. The low cost and ecocompatibility made this process attractive for large-scale preparation

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Qi, Gang; Zhang, Wenguo; Dai, Yong published an article about the compound: 5-(4-Pyridyl)-1H-tetrazole( cas:14389-12-9,SMILESS:C1(C2=NN=NN2)=CC=NC=C1 ).Category: chiral-nitrogen-ligands. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:14389-12-9) through the article.

We report an efficient method of synthesis of 5-substituted 1H-tetrazoles by [2+3] cycloaddition of nitriles and sodium azide with graphene as nonmetal catalyst. Under optimized conditions, moderate to good yields (60-70 %) are obtained. The catalyst can be easily separated by centrifugation.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Reference of 5-(4-Pyridyl)-1H-tetrazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-(4-Pyridyl)-1H-tetrazole, is researched, Molecular C6H5N5, CAS is 14389-12-9, about Solid state coordination chemistry of copper with pyridyltetrazoles: Structural consequences of incorporation of coordinating anions. Author is Darling, Kari; Ouellette, Wayne; Zubieta, Jon.

The hydrothermal reactions of various Cu(II) salts with 3- and 4-pyridyltetrazole and pyrazinyltetrazole were exploited in the preparation of Cu(II) and Cu(I) azolate materials. The parent Cu/pyridyltetrazole compositions are observed in the two-dimensional [Cu(3-pyrtet)2] (1), the reduced three-dimensional [Cu(4-pyrtet)] (2) and reduced two-dimensional [Cu(4-pyrtet)]·0.5DMF (3·0.5DMF) (Hpyrtet = pyridyltetrazole). The consequences of introducing coordinating anions are revealed in the structures of the 1-dimensional [CuCl2(4-Hpyrtet)]·0.5H2O (4·0.5H2O) and the two-dimensional [Cu2I2(4-Hpyrtet)] (5) and [Cu(acac)(4-pyrtet)] (7) (acac = acetylacetonate; H2en = ethylenediammonium cation). The pyrazinyltetrazolate derivative [H2en]0.5[CuCl2(prztet)] (Hprztet = pyrazinyltetrazole) (6) is 1-dimensional, but structurally distinct from the chain observed for 4.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzodiazlnes. VI. Synthesis of 2-substituted-4-hydrazinoquinazolines, 5-substituted [3,4-c]-s-triazolo-, and [1,5-c]tetrazoloquinazolines》. Authors are Postovskii, I. Ya.; Vereschagina, N. N.; Mertsalov, S. L..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Reference of 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.

cf. CA 63, 13256g. 2-R-substituted quinazol-4-ones (I), -4-chloroquinazolines (II), and -4-hydrazinoquinazolines (III) were prepared Treatment of II with CS(NH2)2 gave the corresponding isothiuronium salts, which on treatment with NaOH gave 2-R-substituted-quinazoline-4-thiones (IV). III with HNO2 gave 5-R-substituted[1,5-c]tetrazoloquinazolines (V), with CH(OEt)3 gave 5-R-substituted[3,4-c]-s-triazoloquinazolines (VI). V treated with HCl gave I (a, R = Me) (b, R = Ph) (c, R = α-furyl) (d, R = γ-pyridyl). Thus, 12.5 g. thioisonicotinamide and 12.5 g. anthranilic acid was heated at 150-60° 1 hr. to give 7.5 g. Id, m. 250° (dioxane). IIa-c were prepared according to Scarborough et al. (CA 57, 7263h). IIa m. 86-8° (heptane); IIb m. 124-6° (heptane); IIc m. 122-4° (heptane). A mixture of 7.5 g. Id, 60 cc. POCl3, and 10 g. PCl5 was boiled 4 hrs., POCl3 distilled, the mixture poured onto ice, neutralized with NH3, and filtered, the precipitate washed with H2O and dried, the residue extracted with boiling C6H6, and the extract filtered and evaporated gave 6.5 g., IId, m. 164-6° (heptane). II (0.02 mole) in C6H6 was stirred and cooled, 5-fold excess NH2NH2.H2O in C6H6 added, and the mixture stirred 2 hrs. gave III. II (0.01 mole), 0.01 mole CS(NH2)2, and 50 cc. EtOH boiled 1 hr. and evaporated, the residue dissolved in NaOH, the mixture filtered, and the filtrate acidified with AcOH gave IV. The following III and IV were prepared (R, III m.p., III % yield, IV m.p., and IV % yield given): Me, 180-2° (CHCl3), 80, 217-18° (EtOH), -; Ph, 214-15° (CHCl3), 81, 216-18° (EtOH), 63; α-furyl, 249-50° (dioxane), 76, 219-20° (dioxane), 85; γ-pyridyl, 200-2° (CHCl3,), 97, -, -. Treatment of IIa with NH2NH2.H2O in EtOH gave 50% N,N’-bis(2-methylquinazolyl)-4-hydrazine (VII), m. 280° (isoPrOH). III (0.002 mole) boiled I hr. with 5-fold excess CH(OEt)3 gave VI. NaNO2 (0.002 mole) was added to 0.002 mole III in 2N HCl at 3-5° and the mixture stirred 1 hr. to give V. V were also prepared by treating II with NaN3 in EtOH. The following VI and V were prepared (R, VI m.p., VI % yield, V m.p., and V % yield given): Me, >280°, 50, 163-5°, 60; Ph, 204-6°, 97, 162-3°, 70; α-furyl, 260-2°, 98, 194-6°, 73; γ-pyridyl, 206-7°, 80, 200-2°, 80. Boiling IV with 15-fold excess NH2NH2.H2O in EtOH until no more H2S evolved (8-10 hrs.) gave III. Treatment of V with HCl (1:1) 3 hrs. gave I. The compounds with R = Me differ considerably from the others, both in color and in stability of the intermediate reaction products.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Thakur, Maheshwar S.; Nayal, Onkar S.; Rana, Rohit; Kumar, Manoranjan; Sharma, Sushila; Kumar, Neeraj; Maurya, Sushil K. published an article about the compound: 2-Aminoquinazolin-4(3H)-one( cas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2 ).Application of 20198-19-0. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:20198-19-0) through the article.

A novel, mild and transition metal-free, 2-aminoquinazolin-4(3H)-one-assisted reduction of nitroarenes employing hydrazine hydrate as reducing agent and potassium carbonate as a base is reported. For the first time, the activation of hydrazine hydrate with an organocatalyst has been explored for reduction reactions. Also for the first time, 2-aminoquinazolin-4(3H)-one and its derivatives have been investigated as hydrogen bonding organocatalysts for the reduction of nitroarenes to anilines. Sensitive functional groups such as sulfonamide, carboxyl, amide and halides were well tolerated in this green methodol. with scalability and high chemoselectivity.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Related Products of 20198-19-0. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Aminoquinazolin-4(3H)-one, is researched, Molecular C8H7N3O, CAS is 20198-19-0, about One-carbon compounds as synthetic intermediates. The synthesis of hydropyrimidines and hydroquinazolines by sequential nucleophilic addition to diphenyl cyanocarbonimidate with concomitant cyclization. Author is Garratt, Peter J.; Hobbs, Christopher J.; Wrigglesworth, Roger.

Di-Ph cyanocarbonimidate (PhO)2C:NCN, undergoes nucleophilic addition with ω-amino esters and amines in a sequential manner to give guanidine derivatives that, for the most part, spontaneously cyclize to give hydropyrimidines, e.g. I, or hydroquinazolines. The hydropyrimidines could be dehydrogenated to pyrimidines, and the NCN group could be hydrolyzed to a carbonyl or amine group in the pyrimidine and to an amine group in the quinazoline series. The regiospecificity of the cyclization was determined by a combination of spectroscopic methods and comparison of compounds synthesized by standard routes. The scope of the synthetic route is indicated. Some of the acyclic N-cyano-O-phenylisoureas formed by the first nucleophilic addition exist as mixtures of isomers, and the barriers to interconversion have been determined by NMR spectroscopy.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Aminoquinazolin-4(3H)-one(SMILESS: O=C1NC(N)=NC2=C1C=CC=C2,cas:20198-19-0) is researched.Recommanded Product: 111-24-0. The article 《Chemical Fragments that Hydrogen Bond to Asp, Glu, Arg, and His Side Chains in Protein Binding Sites》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:20198-19-0).

We present an anal. of the chem. fragments from lead-like ligands in the Protein Data Bank (PDB) that form hydrogen bonds to the side chains of Asp, Glu, Arg, and His, which are the most common residues found in ligand binding sites. A fragment is defined as the largest ring assembly containing the atoms involved in hydrogen bonding. In total, 462 fragments were found in 2038 ligands from over 8000 protein-ligand structures in the PDB. The results show which fragments have a higher propensity for interaction with specific side chains. Some fragments interact with Asp but not with Glu, and vice versa, despite these side chains sharing the same chem. moiety. Arg side chains form hydrogen bonds almost exclusively with O-mediated ligands, and the fragments are the most diverse. Hydrogen bond distances from the imidazole of His showed a wider range than the other three amino acids.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis