Category: pyridazine

Electrochemical reduction of azaaromatics. V. Influence of fluorine substitution on the electron affinities was written by Van den Ham, D. M. W.;Harrison, G. F. S.;Spaans, A.;Van der Meer, D.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1975.Synthetic Route of C4H2F2N2 This article mentions the following:

The electrochem. reduction process of fluoro-substituted azaaromatics, e.g., 3,6-difluoropyridazine, is described by the pattern which is normally postulated for aryl halogenides, that is, fission of the C-halogen bond. However, the stability of the intermediate mononegative ions is generally higher than for the comparable fluoro-substituted arenes. As an example of this stability, the ERS spectrum of tetrafluoroquinoxaline is given. The half-wave reduction potentials of the first reduction wave are related to the electron affinities of the molecules. These electron affinities are correlated with those obtained by semi-empirical quantum chem. calculations In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Synthetic Route of C4H2F2N2).

3,6-Difluoropyridazine (cas: 33097-39-1) belongs to pyridazine derivatives. Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. Pyridazine and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Synthetic Route of C4H2F2N2

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Pyridazine series. Absorption spectrum of pyridazine was written by Evans, Richard Castleman;Wiselogle, F. Y.. And the article was included in Journal of the American Chemical Society in 1945.COA of Formula: C5H6N2O This article mentions the following:

α-Oxoglutaric acid (380 g.) in 600 cc. hot H₂O, added to 230 g. tech. NaOH and 340 g. N₂H₄.H₂SO₄ in 1.5 l. H₂O, gives 50% of 1,4,5,6-tetrahydro-6-oxo-3-pyridazinecarboxylic acid (I), m. 195-6°; dehydrogenation of 284 g. of I in 1 l. boiling AcOH with 360 g. tech. Br (several drops per sec.) gives 65% of 1,6-dihydro-6-oxo-3-pyridazinecarboxylic acid (II), m. 257° (decomposition). Decarboxylation of I by melting gives 23% of 4,5-dihydro-3(2)-pyridazone, m. 41-3°; II gives 90% of 3(2)-pyridazone (III), b₁ 146-8°, m. 102°. III (30 g.), treated with 50 cc. POCl₃ and stirred 45 min. at 65-75°, gives 68% of 3-chloropyridazine (IV), which decomposes rapidly at 95°/1 mm.; solutions of IV in EtOH appear to be relatively stable at room temperature IV (24 g.) in 20 cc. concentrated NH₄OH and 50 cc. 95% EtOH and 0.75 g. Pd on Norite A, hydrogenated at room temperature and 45 lb. pressure for 15-30 min., give 5.2 g. pyridazine (V), b₁ 47-8°, b. 205-6°, d₂₀²⁰ 1.111, n_D³⁰ 1.5148. The ultraviolet absorption curves are given for V in hexane and H₂O and for its HCl salt in H₂O. III (15 g.) and 10 g. Me₂SO₄ in 50 cc. MeOH, treated with 8 g. NaOH and refluxed 1 hr., give 2 g. of the 2-Me derivative (VI), hygroscopic, m. 38-9°. IV (12 g.) and MeONa in MeOH give 6 g. of 3-methoxypyridazine (VII), b₅ 77-8°, n_D³⁰ 1.5086; 3-EtO analog, b_2-3 69-71°, m. 35-6°, n_D³⁰ 1.5000, 56% yield. VI is thermally stable but VII slowly decomposes at room temperature In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4COA of Formula: C5H6N2O).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. Pyridazine is bioavailable (especially in the CNS) and can reduce toxicity. Pyridazine is a component of several drug molecules, and the pyridazine pharmacophore has contributed to a variety of pharmacologically active compounds.COA of Formula: C5H6N2O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis of new s-triazolo[4,3-b]pyridazines was written by Francavilla, P.;Lauria, F.. And the article was included in Journal of Heterocyclic Chemistry in 1971.Synthetic Route of C5H3ClN4O This article mentions the following:

A new synthesis of s-triazolo[4,3-b]pyridazine (I) derivatives was achieved starting from 3,6-dichloropyridazine. The method opens the way to substitutions in the 2- or 3-positions. A tricyclo derivative, 3-chloro-6-methyl-(bis-s-triazolo[4,3-b;3′,4′-f]pyridazine) (II), was also synthesized. In the experiment, the researchers used many compounds, for example, 6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (cas: 33050-32-7Synthetic Route of C5H3ClN4O).

6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (cas: 33050-32-7) belongs to pyridazine derivatives. Pyridazine-based compounds continued to be a great source of biologically active compounds as evidenced by the number of publications which emerged in 2021. The activity depends upon the changes of substituted groups in the pyridazine ring system resulting in different biological activities. In addition, the natural pyrimidine bases uracil, thymine, and cytosine, which are constituents of the nucleic acids, are found to be the most important naturally occurring diazines.Synthetic Route of C5H3ClN4O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Scaffold-hopping strategy: synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents was written by Tung, Yen-Shih;Coumar, Mohane Selvaraj;Wu, Yu-Shan;Shiao, Hui-Yi;Chang, Jang-Yang;Liou, Jing-Ping;Shukla, Paritosh;Chang, Chun-Wei;Chang, Chi-Yen;Kuo, Ching-Chuan;Yeh, Teng-Kuang;Lin, Chin-Yu;Wu, Jian-Sung;Wu, Su-Ying;Liao, Chun-Chen;Hsieh, Hsing-Pang. And the article was included in Journal of Medicinal Chemistry in 2011.Application of 19064-65-4 This article mentions the following:

Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 I, an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shuffling of the nitrogen from the N-1 position or by insertion of one or two nitrogen atoms into the indole core of I. Among these, 7-azaindole core II showed potent in vitro anticancer activity and improved oral bioavailability (F = 35%) compared with I (F < 10%). In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Application of 19064-65-4).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazine and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Application of 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

3,6-Bis(4-methoxybenzyloxy)pyridazine was written by Hu, Fang Zhong;Zhang, Min;Song, Hai Bin;Zou, Xiao Mao;Yang, Hua Zheng. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2005.COA of Formula: C4H2F2N2 This article mentions the following:

In the crystal structure of the title compound, C₂₀H₂₀N₂O₄, the mols. are linked by a weak intermol. C-H···N H bond. The mol. has crystallog. 2-fold rotation symmetry. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1COA of Formula: C4H2F2N2).

3,6-Difluoropyridazine (cas: 33097-39-1) belongs to pyridazine derivatives. The pyridazine structure is a popular pharmacophore which is found within a number of herbicides such as credazine, pyridafol and pyridate. The activity depends upon the changes of substituted groups in the pyridazine ring system resulting in different biological activities. In addition, the natural pyrimidine bases uracil, thymine, and cytosine, which are constituents of the nucleic acids, are found to be the most important naturally occurring diazines.COA of Formula: C4H2F2N2

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Proton spin-lattice relaxation on acetic acid was written by Hrynkiewicz, A. Z.;Krynicki, K.;Waluga, I.. And the article was included in Archives des Sciences in 1961.Recommanded Product: 3-Methoxypyridazine This article mentions the following:

By measuring the nuclear resonance absorption at a resonance frequency of 28 Mc., a non-exponential increase of magnetization of protons in liquid AcOH is observed with time of storage at temperatures of 20, 30, 50, and 80°. An explanation for these results is possible on the assumption of different spin-lattice relaxation times for the protons in the CH₃ and in the COOH groups. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Recommanded Product: 3-Methoxypyridazine).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. The unsubstituted pyridazines are more resistant to eletrophilic substitution due to the nature of withdrawal of electron density from the ring by two heteroatoms, while the related electron deficiency of the ring makes pyridazine more easily attacked by nucleophiles.Recommanded Product: 3-Methoxypyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Cooperative Interactions in the Second Coordination Sphere of Pyridazine/Pyridine Containing Polyazaheterocyclic Iron(II) Complexes Favor Protonation was written by Hammoud, Ahmad;Nshimyumuremyi, Jean-Boris;Bourotte, Jeremie;Lucaccioni, Fabio;Robeyns, Koen;Dirtu, Marinela M.;Garcia, Yann;Singleton, Michael L.. And the article was included in European Journal of Inorganic Chemistry in 2018.Reference of 27349-66-2 This article mentions the following:

The new pyridazine containing iron complexes, [N,N,N’,N’-tetrakis(3-pyridazylmethyl)propylenediamine]iron(II)(PF₆)₂ (1) and [N,N’-bis(2-pyridazylmethyl)-N,N’-bis(2-pyridylmethyl)propylenediamine]iron(II) (PF₆)₂ (2) were synthesized and their reactivity towards protonation was compared to that of the analogous tetrapyridine complex [N,N,N’,N’-tetrakis(2-pyridylmethyl)propylenediamine]iron(II)(PF₆)₂ (3). The solution and solid-state structures were confirmed by NMR and x-ray crystallog. studies. For 1–3, the ligands bind in a hexadentate fashion giving similar octahedral structures with an N₆ coordination environment. Across the series, the increasing number of pyridazines has only modest effects on the spectroscopic and electrochem. properties of the metal. Nevertheless, their reactivity towards protonation is drastically different. While 2 and 3 decompose in the presence of strong acids, 1 is able to be stably protonated as a result of cooperative 2nd sphere interactions. In the experiment, the researchers used many compounds, for example, 3-(Chloromethyl)pyridazine hydrochloride (cas: 27349-66-2Reference of 27349-66-2).

3-(Chloromethyl)pyridazine hydrochloride (cas: 27349-66-2) belongs to pyridazine derivatives. Pyridazine and phthalazine have quite different spectroscopic properties compared with their isomers, pyrazine and quinoxaline. The activity depends upon the changes of substituted groups in the pyridazine ring system resulting in different biological activities. In addition, the natural pyrimidine bases uracil, thymine, and cytosine, which are constituents of the nucleic acids, are found to be the most important naturally occurring diazines.Reference of 27349-66-2

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Room-temperature nucleophilic aromatic fluorination: experimental and theoretical studies was written by Sun, Haoran;DiMagno, Stephen G.. And the article was included in Angewandte Chemie, International Edition in 2006.Safety of 3,6-Difluoropyridazine This article mentions the following:

The use of anhydrous tetrabutylammonium fluoride in nucleophilic aromatic substitution reactions, including variants of the selective halogen-exchange and fluorodenitration processes, was investigated. It was shown that TBAF permits these reactions to be performed under surprisingly mild conditions if it is used in relatively nonpolar media. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Safety of 3,6-Difluoropyridazine).

3,6-Difluoropyridazine (cas: 33097-39-1) belongs to pyridazine derivatives. The pyridazine structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. Pyridazine and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Safety of 3,6-Difluoropyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Ab Initio EOM-CCSD Investigation of One-Bond C-C, N-C, and N-N Spin-Spin Coupling Constants in Fluoroazines was written by Del Bene, Janet E.;Alkorta, Ibon;Elguero, Jose. And the article was included in Journal of Physical Chemistry A in 2010.Application of 33097-39-1 This article mentions the following:

Ab initio EOM-CCSD calculations were carried out to examine one-bond ¹J (C-C), ¹J(N-C), and ¹J(N-N) spin-spin coupling constants in benzene, pyridine, the diazines, and selected triazines, tetrazines, and pentazine and their fluoro-substituted derivatives Relative to benzene, ¹J(C-C) decreases in the azines as N atoms are introduced into the ring, but this decrease does not exceed 5 Hz. In the fluoro-substituted derivatives, ¹J(C-C) may increase only slightly if the coupled carbon atoms form C-H bonds, or increase dramatically if either or both of the coupled atoms participate in C-F bonds. The value of ¹J(C-C) also depends on the nature of the bonding of the coupled atoms in the ring. The largest increase is found when both carbons participate in C-F bonds, and both are ortho to N atoms. Relative to pyridine, ¹J(N-C) increases as N atoms are introduced into the ring, with the magnitude of the increase depending on the bonding of the coupled atoms. It is negligible if neither atom is bonded to another N, increases if one of the coupled atoms is bonded to another N atom, and increases further if both are bonded to other N atoms. Fluoro-substitution has an opposing effect on ¹J(N-C), making this coupling constant less pos. or neg. when the coupled C participates in a C-F bond. The decrease in ¹J(N-C) relative to the parent mol. is enhanced if either of the coupled atoms is bonded to another N atom or to another C-F group. A further enhancement occurs if both coupled atoms are so bonded, with the largest increases associated with the bonding scheme in which the coupled C is bonded to another N and the coupled N to another C-F. Fluoro-substitution has a small effect on ¹J(N-C) if the coupled C forms a C-H bond, and on ¹J(N-N). Thus, the effects of fluoro-substitution on one-bond couplings tend to be localized. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Application of 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) belongs to pyridazine derivatives. The pyridazine structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. Pyridazine and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Application of 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Imidazo[1,2-b]pyridazines. I. Some 3-alkoxy-6-halo-2-phenyl-(and 4′-substituted phenyl)imidazo[1,2-b]pyridazines and 3-methoxy-2,6-diphenylimidazo[1,2-b]pyridazine was written by Barlin, Gordon B.. And the article was included in Australian Journal of Chemistry in 1986.Recommanded Product: 33097-39-1 This article mentions the following:

A series of the title imidazopyridazines I (R = F, Cl, Br, Ph; R¹ = Me, Et; R² = H, Cl, Br, MeO; R³ = R⁴ = H) have been prepared from the relevant pyridazin-3-amines and arylglyoxals, followed by O-alkylation of the corresponding imidazo[1,2-b]pyridazin-3(5H)-ones with diazoalkanes. 6-Chloro-3-methoxy-2-phenylimidazo[2,1-a]phthalazine I (R = Cl; R¹ = Me; R² = H; R³R⁴ = CH:CHCH:CH) was prepared similarly. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Recommanded Product: 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) belongs to pyridazine derivatives. Pyridazine and phthalazine have quite different spectroscopic properties compared with their isomers, pyrazine and quinoxaline. Specifically, the pyridazine moiety is an important structural feature of various pharmacologically important compounds with activities like antimicrobial, analgesic, anti-inflammatory, antiplatelet, anticancer, antisecretory, antiulcer, antidepressant, cardiotonic, vasodilator, antiarrhythmic, and hypocholesterolaemic.Recommanded Product: 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem