Month: December 2022

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

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

Study on the synthetic condition of aryloxypyridazinoxy lactates – effect of halides in 3,6-dihalide pyridazines on nucleophilic substitution reaction was written by Hu, Fang-Zhong;Wang, Xiang;Ren, Kang-Tai;Yang, Hua-Zheng. And the article was included in Youji Huaxue in 2002.Related Products of 33097-39-1 This article mentions the following:

The synthetic condition of aryloxypyridazinoxy lactates was studied. Aryloxypyridazinoxy lactates can be obtained by two methods. The effect of halides in 3,6-dihalide pyridazines on nucleophilic substitution reaction was studied, too. Calculation of mol. mechanics and quantum chem. indicated that 3,6-difluoropyridazine had an advantage over other 3,6-dihalide pyridazines when it was treated with nucleophilic reagents and confirmed by the exptl. results. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Related Products of 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) 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 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.Related Products of 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis and herbicidal activity of 3-aryloxy-6-chloro(or fluoro)pyridazines was written by Wang, Zhanping;Hu, Fangzhong;Zou, Xiaomao;Yang, Xiufeng;Yang, Huazheng. And the article was included in Nongyaoxue Xuebao in 2004.HPLC of Formula: 33097-39-1 This article mentions the following:

3-Aryloxy-6-chloro(or fluoro)pyridazines I (X = Cl, F; R = Me, NO₂, Cl, CF₃, NH₂, Br, OMe, COOEt, etc.) were prepared from the condensation of various substituted phenols with starting material 3, 6-dichloropyridazine and its fluorinated derivative, 3, 6-difluoropyridazine in high yields. All compounds were characterized by ¹H NMR and elemental analyses, and some of the compounds were confirmed by IR. Preliminary bioassay indicates that some of the title compounds showed herbicidal activity to some extents against Brassica napus and Echinochloa crus-galli, for example, at 100 μg/mL, the inhibition of compounds I (X = Cl, R = 3-Me, 3-NO₂ and X = F, R = 3-Me) against E. crus-gall are 95.7%, 96.1% and 91.2% , resp. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1HPLC of Formula: 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) 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.HPLC of Formula: 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Studies on diazepines. XIII. Photochemical behavior of pyrazine, pyrimidine, and pyridazine N-imides was written by Tsuchiya, Takashi;Kurita, Jyoji;Takayama, Kazuko. And the article was included in Chemical & Pharmaceutical Bulletin in 1980.Formula: C5H6N2O This article mentions the following:

Photolysis of various diazine N-ethoxycarbonylimides, I (R = H, Me; R¹, R² = H, Me, Ph), II, and III (R³ = R⁴ = H, Me; R³ = MeO, R⁴ = H) prepared from the corresponding diazines, gave the pyrazole derivatives, e.g. IV from pyrazine and pyridmidine N-imides, and the pyrrole derivatives from pyridazine N-imides. These photolyses may proceed by rearrangement to diaziridine intermediates, followed by ring expansion to the corresponding 1,2,5-, 1,2,4-, or 1,2,3-triazepines, which then undergo isomerization to the triazabicyclo[3.2.0]heptadienes, followed by elimination. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Formula: C5H6N2O).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. Pyridazines is a six-membered nitrogen-containing significant heterocycle. It has received considerable interest because of its useful applications as natural products, pharmaceuticals, and various bioactive molecules. Pyridazine compounds have attracted interest in various fields like medicinal, industrial, and agricultural research as they are used for numerous biological activities and other applications.Formula: C5H6N2O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Steric and electronic effects on the ¹H hyperpolarization of substituted pyridazines by signal amplification by reversible exchange was written by Rayner, Peter j.;Burns, Michael j.;Fear, Elizabeth j.;Duckett, Simon b.. And the article was included in Magnetic Resonance in Chemistry in 2021.Electric Literature of C5H6N2O This article mentions the following:

Utility of the pyridazine motif is growing in popularity as pharmaceutical and agrochem. agents. The detection and structural characterization of such materials is therefore imperative for the successful development of new products. Signal amplification by reversible exchange (SABRE) offers a route to dramatically improve the sensitivity of magnetic resonance methods, and we apply it here to the rapid and cost-effective hyperpolarization of substituted pyridazines. The 33 substrates investigated cover a range of steric and electronic properties and their capacity to perform highly effective SABRE is assessed. We find the method to be tolerant to a broad range of electron donating and withdrawing groups; however, good sensitivity is evident when steric bulk is added to the 3- and 6-positions of the pyridazine ring. We optimize the method by reference to a disubstituted ester that yields signal gains of >9000-fold at 9.4 T (>28% spin polarization). In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Electric Literature of C5H6N2O).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. The pyridazine structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. 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.Electric Literature of C5H6N2O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Discovery of imidazopyridine derivatives as novel c-Met kinase inhibitors: Synthesis, SAR study, and biological activity was written by Yang, Yifei;Zhang, Yuan;Yang, Ling Yun;Zhao, Leilei;Si, Lianghui;Zhang, Huibin;Liu, Qingsong;Zhou, Jinpei. And the article was included in Bioorganic Chemistry in 2017.Related Products of 33050-32-7 This article mentions the following:

Receptor tyrosine kinase c-Met acts as an alternative angiogenic pathway in the process and contents of cancers. A series of imidazopyridine derivatives were designed and synthesized according to the established docking studies as possible c-Met inhibitors. Most of these imidazopyridine derivatives displayed nanomolar potency against c-Met in both biochem. enzymic screens and cellular pharmacol. studies. Especially, compound 7 g exhibited the most inhibitory activity against c-Met with IC₅₀ of 53.4 nM and 253 nM in enzymic and cellular level, resp. Following that, the compound 7 g was docked into the protein of c-Met and the structure-activity relationship was analyzed in detail. These findings indicated that the novel imidazopyridine derivative compound 7 g was a potential c-Met inhibitor deserving further investigation for cancer treatment. In the experiment, the researchers used many compounds, for example, 6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (cas: 33050-32-7Related Products of 33050-32-7).

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. 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.Related Products of 33050-32-7

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Pyridazines. XXI. Reaction of 1-methylpyridazinium salts with potassium cyanide was written by Kaneko, Chisato;Tsuchiya, Takashi;Igeta, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1973.Related Products of 19064-65-4 This article mentions the following:

The reaction of pyridazinium sulfates, prepared from the corresponding pyridazines and Me2SO4, with KCN was studied. The pyridazines (I, R = H, Me, MeO; R1 = R2 = H) gave dimers II and III and the pyridazinone IV. 3-Phenylpyridazines (I, R = Ph; R1 = R2 = H, Me) gave the 4-pyridazinenitriles (V) as the main product. Other pyridazines (e.g., I, R = R2 = H, R1 = Me; R = R2 = Me, R1 = H; R = MeO, R1 = H, R2 = Me) gave various cyano- and dicyanopyridazines. The mechanism of their formation were discussed. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Related Products of 19064-65-4).

3-Methoxypyridazine (cas: 19064-65-4) 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. Pyridazine can act as a hydrogen bond acceptor to improve the physicochemical properties of drug molecules by increasing their water solubility, and has a high affinity for complexing with targets due to its dipole moment.Related Products of 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis of pyridazine derivatives. VIII. Imidazo[1,2-b]pyridazines and some tricyclic aza analogs was written by Stanovnik, B.;Tisler, Miha. And the article was included in Tetrahedron in 1967.Reference of 13493-79-3 This article mentions the following:

6-Substituted and 3,6-disubstituted imidazo[1,2-b]pyridazines were prepared Some of these derivatives were used for convenient syntheses of a new azaheterocycle, imidazo[1,2-b]-s-triazolo-[3,4-f]pyridazine (I) and its derivatives Another new heterocyclic system, imidazo [1,2-b]tetrazolo[5,1-f]pyridazine (II) was also prepared 40 references. In the experiment, the researchers used many compounds, for example, 6-Chloroimidazo[1,2-b]pyridazine hydrochloride (cas: 13493-79-3Reference of 13493-79-3).

6-Chloroimidazo[1,2-b]pyridazine hydrochloride (cas: 13493-79-3) belongs to pyridazine derivatives. Pyridazines is a six-membered nitrogen-containing significant heterocycle. It has received considerable interest because of its useful applications as natural products, pharmaceuticals, and various bioactive molecules. 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.Reference of 13493-79-3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis and herbicidal evaluation of 3-N-substituted amino-6-benzyloxypyridazine derivatives was written by Zhang, Min;Hu, Fang-Zhong;Zhao, Ting;Yang, Liu-Qing;Yang, Hua-Zheng. And the article was included in Journal of Heterocyclic Chemistry in 2014.Reference of 33097-39-1 This article mentions the following:

A variety of 3-amino-6-benzyloxypyridazine derivatives I (R¹ = 2-OMe, 3,5-Me₂, 4-NO₂, etc.; R² = NMe₂, piperidin-1-yl, morpholin-4-yl) were designed and synthesized in satisfactory yields. The compound I (R¹ = 4-NO₂; R² = piperidin-1-yl) was further determined by X-ray diffraction crystallog. The synthesized compounds herbicidal activities were evaluated against barnyard grass and rape. Most of the compounds I displayed moderate herbicidal activities against the dicotyledonous plant Brassica campestris L. The most active compounds in the laboratory were also evaluated in the greenhouse. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Reference of 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) 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. Pyridazine can act as a hydrogen bond acceptor to improve the physicochemical properties of drug molecules by increasing their water solubility, and has a high affinity for complexing with targets due to its dipole moment.Reference of 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem