Tag: 100-200

Pyridazines. I. Synthesis and nucleophilic substitution of 3-chloromethylpyridazine was written by Novitskii, K. Yu.;Sadovaya, N. K.;Kas’yanova, E. F.;Semina, L. K.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1970.Recommanded Product: 27349-66-2 This article mentions the following:

To a solution of 15 ml SOCl2 in 20 ml anhydrous CHCl3 was added a solution of 12 g I (R = OH) in 60 ml anhydrous CHCl3 and the whole stirred 2 hr to yield 81% I.HCl (R = Cl) (II.HCl), m. 121-1.5° (EtOAc). This (3.3 g) in 30 ml MeOH was added dropwise to MeONa (from 1.84 g Na) in 30 ml anhydrous MeOH, and the whole stirred 30 min at room temperature and refluxed 4-5 hr to yield 76% I (R = OMe), b11 114-15°, d20 1.0978, n2oD 1.5077; picrate m. 87-8° (aqueous EtOH). Similarly was obtained 55% I (R = OEt), b7 108-9°, d20 1.0543, n20D 1.4990; picrate m. 103-4° (aqueous EtOH). To an emulsion of 0.69 g Na in 2 ml PhMe was added dropwise at 45-50° 3.3 g PhSH, stirring continued 4 hr, II (from 3.3 g II.HCl) in PhMe added, and the whole heated 2 hr on a boiling water bath to yield 96% I (R = SPh), m. 54-5.5° (petroleum ether); picrate m. 112-13° (EtOH). A mixture of 2.5 g II.HCl and 1.2 g (H2N)2CS in 300 ml anhydrous Me2CO was refluxed 10 hr to yield 92% I [R = SC(:NH)NH2.2HCl], m. 187-8° (decomposition) (hexane-MeOH). This (2.5 g) heated 1 hr on a boiling water bath with saturated K2CO3 solution gave 94% I (R = SH). II.HCl and the appropriate amine refluxed 3 hr in ether, C6H6 or in the amine gave the following I (R, b.p., mm, m.p./m.p. dipicrate, and % yield given): NEt2, 124-5°/6,-,145.5-6° (EtOH), 87; morpholino, 130-1°/1, 56-7°, 169-70° (EtOH), 85; 1 pyrrolidinyl, 115°/1.5, 51-2°, 148-9° (EtOH), 96. To a solution of 3.25 g NaCN in 5 ml H2O on a water bath was added 3.3 g II.HCl in 20 ml EtOH, and the whole refluxed 1 hr to yield 46% I (R = CN), m. 90-1° (C6H6); HCl salt m. 132-3° (EtOAc). This (1 g) in 15 ml 10% HCl heated 5 hr at 60° gave 100% I (R = H), m. 191-2° (Me2CO). In the experiment, the researchers used many compounds, for example, 3-(Chloromethyl)pyridazine hydrochloride (cas: 27349-66-2Recommanded Product: 27349-66-2).

3-(Chloromethyl)pyridazine hydrochloride (cas: 27349-66-2) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. 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.Recommanded Product: 27349-66-2

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine was written by Gribble, Michael W.;Liu, Richard Y.;Buchwald, Stephen L.. And the article was included in Journal of the American Chemical Society in 2020.Application of 19064-65-4 This article mentions the following:

Bis(phosphine) copper hydride complexes are uniquely able to catalyze direct dearomatization of unactivated pyridines with carbon nucleophiles, but the mechanistic basis for this result has been unclear. Here we show that, contrary to our initial hypotheses, the catalytic mechanism is monometallic and proceeds via dearomative rearrangement of the phenethylcopper nucleophile to a Cpara-metalated form prior to reaction at heterocycle C4. Our studies support an unexpected heterocycle-promoted pathway for this net 1,5-Cu-migration beginning with a doubly dearomative imidoyl-Cu-ene reaction. Kinetics, substituent effects, computational modeling, and spectroscopic studies support the involvement of this unusual process. In this pathway, the CuL₂ fragment subsequently mediates a stepwise Cope rearrangement of the doubly dearomatized intermediate to the give the C4-functionalized 1,4-dihydropyridine, lowering a second barrier that would otherwise prohibit efficient asym. catalysis. 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 structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. 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.Application of 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Discovery of Reldesemtiv, a Fast Skeletal Muscle Troponin Activator for the Treatment of Impaired Muscle Function was written by Collibee, Scott E.;Bergnes, Gustave;Chuang, Chihyuan;Ashcraft, Luke;Gardina, Jeffrey;Garard, Marc;Jamison, Chris R.;Lu, Kevin;Lu, Pu-Ping;Muci, Alexander;Romero, Antonio;Valkevich, Ellen;Wang, Wenyue;Warrington, Jeffrey;Yao, Bing;Durham, Nickie;Hartman, James;Marquez, Anna;Hinken, Aaron;Schaletzky, Julia;Xu, Donghong;Hwee, Darren T.;Morgans, David;Malik, Fady I.;Morgan, Bradley P.. And the article was included in Journal of Medicinal Chemistry in 2021.HPLC of Formula: 33097-39-1 This article mentions the following:

Herein, the discovery of reldesemtiv I, a second-generation fast skeletal muscle troponin activator (FSTA) that increases force production at submaximal stimulation frequencies, is reported. Property-based optimization of high throughput screening hit, 4-(4-fluorobenzyl)-5-(phenethylamino)-1,2,4-thiadiazole, led to compounds with improved free exposure and in vivo muscle activation potency compared to the first-generation FSTA, tirasemtiv. The compound I demonstrated increased muscle force generation in a phase 1 clin. trial and is currently being evaluated in clin. trials for the treatment of amyotrophic lateral sclerosis. 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. 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. In the past decade, X-ray data were reported with regard to the characterization and structural elucidation of a number of pyridazine-metal complexes, including pyridazine ligands with zinc, nickel, copper, cadmium and ruthenium.HPLC of Formula: 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Ring-closing metathesis for the synthesis of heteroaromatics: evaluating routes to pyridines and pyridazines was written by Donohoe, Timothy J.;Bower, John F.;Basutto, Jose A.;Fishlock, Lisa P.;Procopiou, Panayiotis A.;Callens, Cedric K. A.. And the article was included in Tetrahedron in 2009.Application In Synthesis of 3-Methoxypyridazine This article mentions the following:

Ring-closing olefin metathesis (RCM) has been applied to the efficient synthesis of densely and diversely substituted pyridine and pyridazine frameworks. Routes to suitable metathesis precursors have been investigated and the scope of the metathesis step has been probed. The metathesis products function as precursors to the target heteroaromatic structures via elimination of a suitable leaving group, which also facilitates earlier steps by serving as a protecting group at nitrogen. Further functionalization of the metathesis products is possible both prior to and after aromatization. The net result is a powerful strategy for the de novo synthesis of highly substituted heteroaromatic scaffolds. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Application In Synthesis of 3-Methoxypyridazine).

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. 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.Application In Synthesis of 3-Methoxypyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Photochemistry. VI. Photo-induced methylation of pyridazines was written by Tsuchiya, Takashi;Arai, Heihachiro;Igeta, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1972.Recommanded Product: 19064-65-4 This article mentions the following:

Irradiation of pyridazine (I, R = R1 = H) (MeOH containing 5% HCl) gave II (R = R1 = H) and III (R = R1 = H). I (R = H, R1 = Me) gave II (R = H, R1 = Me; R = Me, R1 = H) and III (R = H, R1 = Me). I (R = MeO, R1 = H) gave II (R = H, R1 = MeO; R = Me, R1 = MeO). I (R = R1 = Me) gave II (R = R1 = Me) and III (R = R1 = Me). I (R = Me, R1 = MeO) gave only II (R = Me, R1 = MeO). I (R = Me, R1 = Cl; R = R1 = Cl; R = Cl, R1 = Ph, gave the 5-methylated and 4,5-dimethylated compounds resp. I (R = Cl, R1 = H) (IV) did not give monomethylation, but gave III (R = Cl, R1 = H) (1-2%), due to decomposition of IV. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Recommanded Product: 19064-65-4).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. Pyridazine and phthalazine have quite different spectroscopic properties compared with their isomers, pyrazine and quinoxaline. In the past decade, X-ray data were reported with regard to the characterization and structural elucidation of a number of pyridazine-metal complexes, including pyridazine ligands with zinc, nickel, copper, cadmium and ruthenium.Recommanded Product: 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Acids of the pyridazine series. I. New preparations of 3-chloro-6-pyridazinyloxyacetic acid and some of its derivatives was written by Rosseels, G.. And the article was included in Bulletin des Societes Chimiques Belges in 1964.Recommanded Product: 3-Methoxypyridazine This article mentions the following:

Treatment of dimethylaminoethylamine with chloroacetyl chloride in EtOAc at 0° led to the hydrochloride of R₂NCH₂CH₂NHCOCH₂Cl (I, R = Me), m. 121°, in 50% yield. Similarly, the hydrochloride of N,N-diethylaminoethyl-2-chloroacetamide (I, R = Et), m. 77° was prepared in 50% yield from diethylaminoethylamine. Treatment of 3,6-dichloropyridazine with glycolic acid in alk. solution afforded 65% 3-chloro-6-pyridazinyloxyacetic acid (II, R = H), m. 145°, 278 mμ (log ε 3.27). Reaction of 3-chloropyridazin-6-one with chloroacetic acid in KOH solution gave 85% 3-chloro-6-oxo-1-pyridazinylacetic acid (III, R = OH), m. 220°, k 300 mμ (log ε 3.47). Et diazoacetate reacts with 3-chloropyridazin-6-one in C₆H₆ in the presence of Cu powder to give a mixture of Et 3-chloro-6-pyridazinyloxyacetate (II, R = Et), b_0.2 120-4°, m. 67° (60%), and Et 3-chloro-6-oxo-1-pyridazinylacetate (III, R = OEt), b_0.2 131-5°, m. 78° (6.7%). The major product (II, R = Et) was identified by the similarity of its ultraviolet and infrared spectra to those of II (R = H) to which it was converted by alk. hydrolysis. Esterification of II (R = H) with EtOH and H₂SO₄ gave II (R = Et) which was identical with the product from the diazoacetate reaction. Et glycolate reacted with 3,6-dichloropyridazine to give II (R = Et) directly in 60% yield. The minor product (III, R = OEt) was similarly identified by its spectra and hydrolysis to 3-chloro-6-oxo-1-pyridazinylacetic acid (III, R = OH) which was reesterified to give III (R = OEt), which was independently prepared by the action of Et chloroacetate on 3-chloropyridazin-6-one. Attempts to chlorinate 3-oxo-6-pyridazinylacetic acid with POCla led only to 3-chloropyridazin-6-one, m. 140°. Treatment with POCl₃ of 3-hydroxy-6-oxo-1-pyridazinylacetic acid gave 3,6-dichloropyridazine. Reaction of II (R = H) with 2-chloro-1-dimethylaminoethane (IV) in iso-PrOH led, in 60% yield, to dimethylaminoethyl 3-chloro-6-pyridazinyloxyacetate (II, R = CH₂CH₂NMe₂) hydrochloride, m. 120°, X 275 mμ (log ε 3.240). Similarly, II (R = H) was converted to the hydrochloride of II (R = CH₂CH₂NEt₂), m. 118°, in 50% yield, by reaction with 2-chloro-1-diethylaminoethane (V). Treatment of III (R = OH) with IV or V led to the hydrochloride of III (R = CH₂CH₂NMe₂), m. 120°, in 60% yield or the hydrochloride of III (R = CH₂CH₂NEt₂), m. 118°, in 58% yield, resp. Reaction of IV with 3-oxo-6-pyridazinyloxyacetic acid and working up with tartaric acid led to the tartrate of dimethylaminoethyl 3-oxo-6pyridazinyloxyacetate, m. 314° (decomposition), in 50% yield. Similarly, the tartrate of dimethylaminoethyl 3-hydroxy-6-oxo-1-pyridazinylacetate, m. 310° (decomposition), was prepared in 51% yield from 3-hydroxy-6-oxo-1-pyridazinylacetic acid and IV and working up with tartaric acid. The hydrochloride of the β-dimethylaminoethylamide of 3-chloro-6-oxo-1-pyridazinylacetic acid (III, R = NHCH₂CH₂NMe₂.HCl), m. 263°, was prepared in 50% yield from I (R = Me) and 3-chloropyridazin-6-one. Similarly, III (R = NHCH₂CH₂NEt₂.HCl), m. 258°, was prepared in 50% yield from I (R = Et) and 3-chloropyridazin-6-one. 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. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. 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: 3-Methoxypyridazine

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

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

Pyridazines. XXIII. Synthesis of N-substituted 1,4-dihydropyridazines was written by Kaneko, Chisato;Tsuchiya, Takashi;Igeta, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1974.Recommanded Product: 3-Methoxypyridazine This article mentions the following:

1-Methylpyridazinium salts, derived from pyridazines I to VI, were reduced with NaBH4 to give the corresponding 1-methyl-1,6-dihydropyridazines VII in 40-60% yields. Pyridazines I to VI were reduced with NaBH4 in the presence of MeO2CCl to afford 1-methoxycarbonyl-1,6-dihydropyridazines VIII and their 1,4-isomers IX, in total 35-65% yields, ratio of which depended on the kinds of the substituents. Thus, I gave little of the corresponding IX, while V gave little VIII. 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. 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.Recommanded Product: 3-Methoxypyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Selective fluorination by halogen exchange of chlorodiazines and chloropyridines promoted by the ‘proton sponge’-triethylamine tris(hydrogen fluoride) system was written by Darabantu, M.;Lequeux, T.;Pommelet, J.-C.;Ple, N.;Turck, A.. And the article was included in Tetrahedron in 2001.Name: 3,6-Difluoropyridazine This article mentions the following:

The ‘proton sponge’-triethylamine tris(hydrogen fluoride) mixtures provide a mild and efficient fluorinating reagent to introduce selectively fluorine atoms by halogen exchange into chlorodiazines and chloronitropyridine series. The PS/Et₃N.3HF mixtures provide an efficient reagent to realize a selective fluorination of various π-deficient chlorinated heterocycles: (benzo)diazines and pyridines. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Name: 3,6-Difluoropyridazine).

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 and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Name: 3,6-Difluoropyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem