Day: April 13, 2022

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.

This literature about this compound(20198-19-0)Reference of 2-Aminoquinazolin-4(3H)-onehas given us a lot of inspiration, and I hope that the research on this compound(2-Aminoquinazolin-4(3H)-one) can be further advanced. Maybe we can get more compounds in a similar way.

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

Kou, Yuan; Yin, Yuanqi published an article about the compound: Tri(naphthalen-1-yl)phosphine( cas:3411-48-1,SMILESS:C1=CC2=C(C=C1)C(=CC=C2)P(C1=CC=CC2=C1C=CC=C2)C1=CC=CC2=C1C=CC=C2 ).Synthetic Route of C30H21P. 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:3411-48-1) through the article.

Hydroformylation of camphene in the presence of [(COD)-RhCl]2 and various phosphine ligands under 10 MPa syngas (CO/H2 = 1), 100 °C has been investigated. The active catalyst has been demonstrated by the IR spectra to be the HRh(CO)Ln (for bidentates, n = 1, for monodentates, n = 2). The selectivity to exo- or endo-products (aldehyde and/or alc.) is found to be decided by the cone angle of the ligand carried by the rhodium carbonyl. The larger ligands such as P(o-tolyl)3 tend to make the rhodium complex approach the double bond from endo side and then to give more exo-alc. because of the attack of the hydrogen occurs from the cis position with the complex. The bidentate phosphine ligands which have relatively smaller cone angles, are expected to give more endo-product. However, the enhanced stability of Rh-Rh bond that arises from the formation of the phosphine-bridged bimetallic rhodium carbonyls limits the formation of the chelated active species, so that only the endo-aldehydes with relatively lower conversion are observed The possible mechanism of exo- and endo-product formations has also been discussed.

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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

Safety of 1,5-Dibromopentane. 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: 1,5-Dibromopentane, is researched, Molecular C5H10Br2, CAS is 111-24-0, about Crystal structure and halogen-hydrogen bonding of a Delepine reaction intermediate. Author is Mulrooney, David Z. T.; Muller-Bunz, Helge; Keene, Tony D..

The reaction of 1,5-dibromopentane with urotropine results in crystals of the title mol. salt, 5-bromourotropinium bromide [systematic name: 1-(5-bromopentyl)-3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane bromide], C11H22BrN4+·Br- (1), crystallizing in space group P21/n. The packing in compound 1 is directed mainly by H···H van der Waals interactions and C-H···Br hydrogen bonds, as revealed by Hirshfeld surface anal. Comparison with literature examples of alkylurotropinium halides shows that the interactions in 1 are consistent with those in other bromides and simple chloride and iodide species.

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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

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

Synthetic Route of C30H21P. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Tri(naphthalen-1-yl)phosphine, is researched, Molecular C30H21P, CAS is 3411-48-1, about The hydroformylation of conjugated dienes. VI. Tertiary aryl- and arylalkylphosphines and secondary alkyl- and arylphosphines as ligands in the rhodium-catalyzed hydroformylation reaction of conjugated dienes to dialdehydes. Author is Bahrmann, H.; Fell, B..

The dependence of the formation of products and isomers on the phosphine used was studied in the title Rh-catalyzed hydroformylation of 1,3-butadiene to dialdehydes. Product formation is directed by a complex combination of steric and electronic factors in the tertiary phosphines. Secondary phosphines are also good cocatalysts for the hydroformylation of butadiene. They lead to an almost complete 1,4-hydroformyl-addition route to the 1,3-diene in the primary step of the hydroformylation of conjugated dienes.

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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

Application In Synthesis of 1,2-Bis(diphenylphosphino)ethane. 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: 1,2-Bis(diphenylphosphino)ethane, is researched, Molecular C26H24P2, CAS is 1663-45-2, about Nano cadmium(II)-benzyl benzothiazol-2-ylcarbamodithioate complexes: Synthesis, characterization, anti-cancer and antibacterial studies.

Benzyl benzothiazol-2-ylcarbamodithioate (BBCT) was used as a ligand for the synthesis of [Cd(BBCT)(PPh3)Cl]Cl (1), [Cd2(BBCT)2(μ-dppm)2]Cl4 (2), or [Cd(BBCT)(phosphine)]Cl2 (where phosphine is dppe (3), dppp (4), dppb (5)) and [Cd(BBCT)(amine)]Cl2 (where amine is bipy (6) or phen (7)). The characterizations (molar conductivity, elemental anal., IR spectra and 31P NMR, 1H NMR and 13C NMR spectra) prove that BBCT ligand behaves as a bidentate ligand through the N atom of thiazole ring group and S atom of thion group while the phosphines or amines ligands behave as bidentate ligand through the P atoms or N atoms, resp. Furthermore, the nanostructure of (1) and (7) was examined by SEM and the results demonstrate the presence of regular nanostructures. The complex (1) shows fiber-grip-like geometry with 85-110 nm while complex (7) shows spiny-flowers-like nanostructures with the flower-forming spines within the range of 80-190 nm. The antibacterial activity of the complexes (1, 2, 3, 6, 7) against S.Epidermidis, S. aureus (gram-pos.) and C.Freundii (gram-neg.) was examined using amikacin as a pos. control. However, all the complexes showed a high ability to inhibit the bacterial species studied, and the inhibition zone was better than that obtained with amikacin. Moreover, the anti-cancer activity of the complexes (1) and (7) against ovarian cancer cell was studied and the results show that both complexes gave cell viability values less than 6%.

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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

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