November 2022 | Page 37 of 38 | Heterocyclic Building Blocks-Naphthyridine

Hamidian, H.’s team published research in Asian Journal of Chemistry in 25 | CAS: 116-63-2

Asian Journal of Chemistry published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C10H9NO4S, Quality Control of 116-63-2.

Hamidian, H. published the artcileSynthesis of new 1,3,4-thiadiazole derivatives containing of morpholine ring, Quality Control of 116-63-2, the publication is Asian Journal of Chemistry (2013), 25(1), 487-489, database is CAplus.

The synthesis of new of 1,3,4-thiadiazole derivatives containing of morpholine ring were investigated. In this study, the derivatives of naphthol, amine and phenol were reacted with morpholine-4-carbonyl chloride. Then, prepared solutions were added to diazotized 2-amino-5-mercapto-1,3,4-thiadiazole to give 2-amino-5-mercapto-1,3,4-thiadiazole products. These dyes were characterized by elemental anal. and spectral analyses (IR, ¹H NMR, ¹³C NMR and mass spectra).

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Goswami, Shyamaprosad’s team published research in Synthetic Communications in 33 | CAS: 14903-78-7

Synthetic Communications published new progress about 14903-78-7. 14903-78-7 belongs to naphthyridine, auxiliary class 6.6_Aromatics,Naphthyridines, name is 2,7-Dimethyl-1,8-naphthyridine, and the molecular formula is C10H10N2, Category: naphthyridine.

Goswami, Shyamaprosad published the artcileMicrowave assisted improved synthesis of 6-formylpterin and other heterocyclic mono- and di-aldehydes, Category: naphthyridine, the publication is Synthetic Communications (2003), 33(3), 475-480, database is CAplus.

2-Pivaloylamino-6-formylpterin (1a) and a series of other important heterocyclic aldehydes have been synthesized in good yield by microwave assisted selenium dioxide oxidation Interestingly, 2-methylpyrazine gives 2-pyrazinecarboxylic acid under the similar condition.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

El-Tabl, Abdou Saad’s team published research in Journal of Chemical, Biological and Physical Sciences in 5 | CAS: 116-63-2

Journal of Chemical, Biological and Physical Sciences published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C10H9NO4S, Recommanded Product: 4-Amino-3-hydroxynaphthalene-1-sulfonic acid.

El-Tabl, Abdou Saad published the artcileSynthesis, characterization and antimicrobial activity of new binary metal complexes derived from amino sulfo-naphthalene ligand, Recommanded Product: 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, the publication is Journal of Chemical, Biological and Physical Sciences (2015), 5(4), 3629-3644, database is CAplus.

New binary metal (II) complexes derived from amino sulfo-naphthalene ligand were prepared The ligand and the metal complexes were characterized from elemental anal., molar conductance, magnetic susceptibility, IR, electronic, ¹H-NMR, and mass spectral studies. Structural and spectroscopic properties revealed that the ligand adopted a tridentate fashion, while the metal complexes adopted a tetragonal distorted octahedral geometry around metal ions. All the complexes are nonelectrolytic in nature as suggested by molar conductance measurements. IR spectral data indicate the coordination between ligand and central metal ion through a phenolic OH, 1-imine N, one oxime-N atoms forming five-membered rings including the metal ions. The compounds were screened for their antimicrobial activities against Aspergillus funigatus, Streptococcs pneumoniae, Bacillis subtilis, Escherichia coli, Pseudomonas coli and candida albicans. Neither the ligand nor its metal complexes recorded antimicrobial activity against neither Pseudomonas coli nor Candida albicans. However, all compounds including the ligand showed high activity against Aspergillus funigatus, Streptococcs pneumoniae, Bacillis subtilis, and Escherichia coli.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Shahroosvand, Hashem’s team published research in Dalton Transactions in 43 | CAS: 116-63-2

Dalton Transactions published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C8H5IO, Application In Synthesis of 116-63-2.

Shahroosvand, Hashem published the artcileRed electroluminescence of ruthenium sensitizer functionalized by sulfonate anchoring groups, Application In Synthesis of 116-63-2, the publication is Dalton Transactions (2014), 43(24), 9202-9215, database is CAplus and MEDLINE.

Five novel Ru(II) phenanthroline complexes with an addnl. aryl sulfonate ligating substituent at the 5-position were synthesized: [Ru(L)(bpy)₂](BF₄)₂ (1), [Ru(L)(bpy)(SCN)₂] (2), [Ru(L)₃](BF₄)₂ (3), [Ru(L)₂(bpy)](BF₄)₂ (4) and [Ru(L)(BPhen)(SCN)₂] (5) (L = (6-one-[1,10]phenanthroline-5-ylamino)-3-hydroxynaphthalene-1-sulfonic acid, bpy = 2,2′-bipyridine, BPhen = 4,7-diphenyl-1,10-phenanthroline), as both photosensitizers for oxide semiconductor solar cells (DSSCs) and light emitting diodes (LEDs). The absorption and emission maxima of these complexes red shifted upon extending the conjugation of the phenanthroline ligand. Ru phenanthroline complexes exhibit broad metal to ligand charge transfer-centered electroluminescence (EL) with a maximum near 580 nm. A particular structure (2) can be considered as both DSSC and OLED devices. The efficiency of the LED performance can be tuned by using a range of ligands. Device (2) has a luminance of 550 cd m^-2 and maximum efficiency of 0.9 cd A^-1 at 18 V, which are the highest values among the 5 devices. The turn-on voltage of this device is ∼5 V. The role of auxiliary ligands in the photophys. properties of Ru complexes was studied by DFT calculation Photovoltaic properties were studied of dye-sensitized nanocrystalline semiconductor solar cells based on Ru phenanthroline complexes and an I redox electrolyte. A solar energy to electricity conversion efficiency (η) of 0.67% was obtained for Ru complex (2) under standard AM 1.5 irradiation with a short-circuit photocurrent d. (J_sc) of 2.46 mA cm^-2, an open-circuit photovoltage (V_oc) of 0.6 V, and a fill factor (ff) of 40%, which are all among the highest values for Ru sulfonated anchoring groups reported so far. Monochromatic incident photon to current conversion efficiency was 23% at 475 nm. Photovoltaic studies clearly indicated dyes with 2 SCN substituents yielded a higher J_sc for the cell than dyes with a tris-homoleptic anchor substituent.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Mohamed, E. A.’s team published research in Journal of the Serbian Chemical Society in 1993 | CAS: 59514-93-1

Journal of the Serbian Chemical Society published new progress about halonaphthyridinedione preparation reaction. 59514-93-1 belongs to class naphthyridine, name is 4-Chloro-1,8-naphthyridin-2(1H)-one, and the molecular formula is C8H5ClN2O, Name: 4-Chloro-1,8-naphthyridin-2(1H)-one.

Mohamed, E. A. published the artcileSynthesis and reactions of 3-halo-1,8-naphthyridine-2,4-diones, Name: 4-Chloro-1,8-naphthyridin-2(1H)-one, the main research area is halonaphthyridinedione preparation reaction.

4-Hydroxy-1,8-naphthyridin-2-one underwent halogenation under different conditions; reactions of the halo compounds with o-phenylenediamine, ethylene glycol, piperidine, hydrazine hydrate, and hydroxylamine were then studied. The structures of all the new compounds synthesized were established by chem. and spectral data.

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

Van den Haak, H. J. W.’s team published research in Recueil: Journal of the Royal Netherlands Chemical Society in 1983-04-30 | CAS: 67988-50-5

Recueil: Journal of the Royal Netherlands Chemical Society published new progress about Amination. 67988-50-5 belongs to class naphthyridine, name is 2,7-Naphthyridin-1(2H)-one, and the molecular formula is C8H6N2O, Computed Properties of 67988-50-5.

Van den Haak, H. J. W. published the artcileσ Adducts. Part 34. Naphthyridines. Part 18. Tele substitutions. Part 18. The amination of halo-2,7- and 1,8-naphthyridines, Computed Properties of 67988-50-5, the main research area is halonaphthyridine amination mechanism; tele substitution naphthyridine halo.

The conversion of 1-halo-2,7-naphthyridines to the corresponding 1-amino compounds with KNH2/NH3, is shown, by the use of deuterated starting compounds, to proceed via an SN(AE)ipso substitution and not via an SN(AE)tele mechanism, even though convincing evidence for the formation of tele σ-adduct, 8-amino-1-halodihydro-2,7-naphthyridine, was obtained. Using the same methods, it is shown that the conversion of 2-bromo-1,8-naphthyridine to 2-amino-1,8-naphthyridine proceeds to the extent of 40% via an odd SN(AE)tele pathway.

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

Baldwin, J. J.’s team published research in Journal of Organic Chemistry in 1978 | CAS: 67988-50-5

Journal of Organic Chemistry published new progress about Cyclization. 67988-50-5 belongs to class naphthyridine, name is 2,7-Naphthyridin-1(2H)-one, and the molecular formula is C8H6N2O, Name: 2,7-Naphthyridin-1(2H)-one.

Baldwin, J. J. published the artcileA novel naphthyridinone synthesis via enamine cyclization, Name: 2,7-Naphthyridin-1(2H)-one, the main research area is naphthyridinol; cyanomethylpyridine cyclocondensation DMF; methylcyanopyridine cyclocondensation DMF; pyridinecarbonitrile methyl DMF cyclocondensation.

I, II, and III are prepared by the reaction of Me2NCH(OMe)2 with vicinal-substituted methylcyanopyridines, e.g., 4-methyl-3-cyanopyridine. The initial condensation is followed by ring closure of the intermediate enamines IV with HBr/AcOH. The method is especially useful for I and II, which previously had been prepared by cumbersome and low-yielding procedures.

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

Guemues, Selcuk’s team published research in Computational & Theoretical Chemistry in 2011-02-28 | CAS: 67988-50-5

Computational & Theoretical Chemistry published new progress about Aromaticity. 67988-50-5 belongs to class naphthyridine, name is 2,7-Naphthyridin-1(2H)-one, and the molecular formula is C8H6N2O, Related Products of naphthyridine.

Guemues, Selcuk published the artcileThe aromaticity of substituted diazanaphthalenes, Related Products of naphthyridine, the main research area is aromaticity diazanaphthalene.

Substituted (F, Cl, OH) diazanaphthalene derivatives were considered theor. to obtain information about their stabilities and aromaticities. The expected decrease of aromaticity of naphthalene itself by double aza substitution was compensated by substitution of one of the hydrogens of the system by an electroneg. atom. The position of the substituent is strongly effective on the aromaticity of the structure such that, the aromaticity is enhanced when the substituent is closer to the aza points.

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

Ziegler, Dorothee S.’s team published research in Organic Letters in 2017-11-03 | CAS: 67988-50-5

Organic Letters published new progress about Electrophiles. 67988-50-5 belongs to class naphthyridine, name is 2,7-Naphthyridin-1(2H)-one, and the molecular formula is C8H6N2O, SDS of cas: 67988-50-5.

Ziegler, Dorothee S. published the artcileDirected Zincation or Magnesiation of the 2-Pyridone and 2,7-Naphthyridone Scaffold Using TMP Bases, SDS of cas: 67988-50-5, the main research area is zincation magnesiation pyridone naphthyridone methoxyethoxymethyl tetramethylpiperidyl base electrophile.

A regioselective zincation of the 2-pyridone and 2,7-naphthyridone scaffolds has been developed. Zincations of the methoxyethoxymethyl (MEM)-protected compounds using TMP2Zn·2MgCl2·2LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by trapping with electrophiles provided functionalized 2-pyridones, e.g. I, and 2,7-naphthyridones, e.g. II. I/Mg exchange of iodinated 2-pyridone and 2,7-naphthyridone using i-PrMgCl·LiCl afforded magnesiated intermediates that reacted with electrophiles. A second magnesiation of the 2-pyridone scaffold was achieved by using TMPMgCl·LiCl. Addnl., CoCl2-catalyzed cross-couplings of the 1-chloro-2,7-naphthyridines with arylzinc halides is reported.

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

Tasker, Nikhil R.’s team published research in Organic & Biomolecular Chemistry in 2019 | CAS: 67988-50-5

Organic & Biomolecular Chemistry published new progress about Antitumor agents. 67988-50-5 belongs to class naphthyridine, name is 2,7-Naphthyridin-1(2H)-one, and the molecular formula is C8H6N2O, Formula: C8H6N2O.

Tasker, Nikhil R. published the artcileIn-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors, Formula: C8H6N2O, the main research area is iminothienopyridinedione preparation photooxygenation PTP4A3 phosphatase inhibitor SAR continuous flow.

A continuous flow photooxygenation of 7-aminothieno[3,2-c]pyridin-4(5H)-ones to produce 7-iminothieno[3,2-c]pyridine-4,6(5H,7H)-diones has been developed, utilizing ambient air as the sole reactant. N-H Imines are formed as the major products, and excellent functional group tolerance and conversion on gram-scale without the need for chromatog. purification allow for facile late-stage diversification of the aminothienopyridinone scaffold. Several analogs exhibit potent in vitro inhibition of the cancer-associated protein tyrosine phosphatase PTP4A3, and the SAR supports an exploratory docking model.

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