Category: pyridazine

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about One-Step Synthesis of 2-Amino-5H-pyrimido[5,4-b]indoles, Substituted 2-(1,3,5-triazin-2-yl)-1H-indoles, and 1,3,5-Triazines from Aldehydes, the main research direction is haloindole carbaldehyde guanidine hydrochloride copper catalyzed cascade cyclization; aminopyrimidoindole preparation; indole carbaldehyde benzaldehyde amidine hydrochloride oxidative cyclization; triazinylindole aryltriazine preparation.Recommanded Product: 5-Methoxy-1H-indole-2-carbaldehyde.

An efficient one-step synthesis of 2-amino-5H-pyrimido[5,4-b]indoles through a copper-catalyzed cascade reaction between 3-haloindole-2-carbaldehydes and guanidine hydrochloride is described. In contrast, the base-mediated reactions of either 3-haloindole-2-carbaldehydes or substituted indole-2-carbaldehydes with substituted amidine hydrochlorides in DMSO result in the formation of 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in one step in excellent yields. Studies toward exploring the utility of the method demonstrate that even substituted benzaldehydes undergo a similar reaction to efficiently yield 2,4,6-trisubstituted 1,3,5-triazines. A plausible mechanism for the formation of substituted 1,3,5-triazines identifies the role of DMSO as an oxidant during the reaction.

From this literature《One-Step Synthesis of 2-Amino-5H-pyrimido[5,4-b]indoles, Substituted 2-(1,3,5-triazin-2-yl)-1H-indoles, and 1,3,5-Triazines from Aldehydes》,we know some information about this compound(21778-81-4)Recommanded Product: 5-Methoxy-1H-indole-2-carbaldehyde, but this is not all information, there are many literatures related to this compound(21778-81-4).

Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ) is researched.Reference of 5-Methoxy-1H-indole-2-carbaldehyde.Zhang, Jian; Gao, Yan-Shan; Gu, Bu-Ming; Yang, Wu-Lin; Tian, Bo-Xue; Deng, Wei-Ping published the article 《Cooperative N-heterocyclic Carbene and Iridium Catalysis Enables Stereoselective and Regiodivergent [3 + 2] and [3 + 3] Annulation Reactions》 about this compound( cas:21778-81-4 ) in ACS Catalysis. Keywords: pyrroloindole preparation enantioselective diastereoselective regioselective; indolyl allyl carbonate enal cyclization carbene iridium catalyst; formylcyclopropane enal cyclization carbene iridium catalyst; pyridineindole preparation enantioselective diastereoselective regioselective; enal indolyl allyl carbonate cyclization carbene iridium catalyst. Let’s learn more about this compound (cas:21778-81-4).

A cooperative N-heterocyclic carbene (NHC)/iridium catalysis has been developed to achieve highly stereoselective and regiodivergent [3 + 2] and [3 + 3] annulation reactions of 2-indolyl allyl carbonates I (R = H, Me; R1 = H, OMe, Me, F, Cl; R1 = H, OMe, Cl) with enals R3CH=CHCHO (R1 = Ph, hexyl, 4-chlorophenyl, furan-2-yl, etc.). The use of the NHC catalyst has introduced switchable homoenolate and enolate intermediates from the common enal precursor via a simple adjustment of reaction conditions in a predictable manner. This protocol furnishes two types of biol. important products, pyrrolo[1,2-a]indoles II and pyridine[1,2-a]indoles III, with high diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Notably, all four stereoisomers of these products with two vicinal stereocenters could be afforded through permutations of the enantiomers of the two chiral catalysts. Mechanistic investigations and further computational d. functional theory calculations give an explanation of the origin of the regioselectivity. In addition, the NHC-enolate intermediate generated from formylcyclopropanes IV (R4 = Ph, tert-Bu, naphthalen-2-yl, etc.) was also compatible in this cooperative catalytic system and thus the arsenal of optically pure pyrrolo[1,2-a]indole products V was enriched.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance, published in 2014-08-01, which mentions a compound: 21778-81-4, mainly applied to pyridoindolone indolizinone enantioselective chemoselective preparation; enantioselective rhodium catalyzed hydroacylation alkenylindolecarboxaldehyde alkenylpyrrolecarboxaldehyde without chelation assistance; bromopyridoindolone preparation mol crystal structure, Safety of 5-Methoxy-1H-indole-2-carbaldehyde.

In the presence of [Rh(1,5-COD)Cl]2, AgBF4, and (R)-2,2′-bis[di(4-methylphenylphenyl)phosphino]-1,1′-binaphthyl [(R)-Tol-BINAP], alkenylindolecarboxaldehydes such as I (R = Me, Et, BuCH2CH2, PhCH2, Ph, 4-MeC6H4, 4-ClC6H4, EtO2C; R1 = H, Et) and N-alkenylpyrrolecarboxaldehydes underwent enantioselective hydroacylation to give tetrahydropyridoindolones such as II (R = Me, Et, BuCH2CH2, PhCH2, Ph, 4-MeC6H4, 4-ClC6H4, EtO2C; R1 = H, Et) or indolizinones in 23-98% yields and in 92-99% ee; the enantioselective cyclizations did not require chelation or other functional groups to facilitate cyclization. The structure of II (R = Me; R1 = Br) was determined by X-ray crystallog.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Application of 17739-45-6. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Bacillus pasinlerensis sp. nov., a thermophilic bacterium isolated from a hot spring in Turkey. Author is Baltaci, Mustafa Ozkan; Ay, Hilal; Akbulut, Sumeyya; Adiguzel, Gulsah; Albayrak, Seyda; Omeroglu, Mehmet Akif; Ozkan, Hakan; Taskin, Mesut; Adiguzel, Ahmet.

A Gram-reaction-pos., endospore-forming bacterium, designated strain P1T, was isolated from water samples collected from Pasinler Hot Spring and characterized using a polyphasic approach to clarify its taxonomic position. Strain P1T was found to have chemotaxonomic and morphol. characteristics consistent with its classification in the genus Bacillus. The strain shared the highest 16S rRNA gene sequence identity values with Bacillus thermolactis R-6488T (97.6%) and Bacillus kokeshiiformis MO-04T (97.2%) and formed a distinct clade with both type strains in the phylogenetic trees based on 16S rRNA gene sequences. Strain P1T could grow optimally at 55 °C and in the presence of 2% NaCl. The organism was found to contain meso-diaminopimelic acid as the diagnostic diamino acid in the cell-wall peptidoglycan. The major polar lipids were diphosphatidylglycerol and phosphatidylglycerol. The predominant menaquinone was determined to be MK-7. The major cellular fatty acids were identified as iso-C15 : 0, iso-C17 : 0 and anteiso-C17 : 0. Based upon the consensus of phenotypic and phylogenetic analyses, strain P1T represents a novel species of the genus Bacillus, for which the name Bacillus pasinlerensis sp. nov. is proposed. The type strain is P1T (= DSM 107529T = CECT 9885T = NCCB 100674T).

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

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.Jaffar, Mohammed; Naylor, Matthew A.; Robertson, Naomi; Lockyer, Stacey D.; Phillips, Roger M.; Everett, Steven A.; Adams, Gerald E.; Stratford, Ian J. researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Formula: C10H9NO2.They published the article 《5-Substituted analogs of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) and their regioisomers as hypoxia-selective agents: structure-cytotoxicity in vitro》 about this compound( cas:21778-81-4 ) in Anti-Cancer Drug Design. Keywords: hydroxymethylaziridinylindoledionepropenol preparation hypoxia selective agent; indoledionepropenol hydroxymethylaziridinyl preparation hypoxia selective agent; aziridinylindoledionepropenol hydroxymethyl preparation hypoxia selective agent. We’ll tell you more about this compound (cas:21778-81-4).

A series of regioisomeric analogs of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) with the hydroxymethyl and hydroxypropenyl substituents situated at either the 2- or the 3-position of the indole ring were synthesized. The compound lacking the 2-hydroxypropenyl substituent had similar properties to EO9 under both aerobic and hypoxic conditions against V79 cells and was more potent against a human tumor cell line (A549) than EO9. It was reduced by human DT-diaphorase (DTD) at more than double the rate of EO9, thus implicating the importance of the enzyme activation step. The compound lacking the 3-hydroxymethyl substituent was a better substrate for human DTD than EO9, yet exhibited lesser toxicity under both aerobic and hypoxic conditions. The toxicity of EO9 was attributed to a combination of the aziridinyl group and the leaving group properties of the 3-hydroxymethyl substituent. In general, compounds with a 5-methylaziridinyl moiety, such as EO8, exhibited substantially better hypoxia-selectivity due to much slower reduction by DTD (20-fold), thus reducing aerobic potency. All compounds had similar electron affinities, as indicated by their one-electron reduction potentials.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Electric Literature of C7H13BrO2. 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: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Novel 18F-Labeled Isonicotinamide-Based Radioligands for Positron Emission Tomography Imaging of Glycogen Synthase Kinase-3β. Author is Zhong, Yuhua; Yang, Shaoxi; Cui, Jianyu; Wang, Jie; Li, Lin; Chen, Yilin; Chen, Junjie; Feng, Pengju; Huang, Shun; Li, Hongsheng; Han, Yanjian; Tang, Ganghua; Hu, Kongzhen.

Glycogen synthase kinase-3β (GSK-3β), a cytoplasmic serine/threonine protein kinase, is involved in several human pathologies including Alzheimer’s disease, bipolar disorder, diabetes, and cancer. Positron emission tomog. (PET) imaging of GSK-3β could aid in investigating GSK-3β levels under normal and pathol. conditions. In this study, we designed and synthesized fluorinated PET radioligands starting with recently identified isonicotinamide derivatives that showed potent affinity to GSK-3β. After extensive in vitro inhibitory activity assays and analyzing U87 cell uptake, we identified [18F]10a-d as potential tracers with good specificity and high affinity. They were then subjected to further in vivo evaluation in rodent brain comprising PET imaging and metabolism studies. The radioligands [18F]10b-d penetrated the blood-brain barrier and accumulated in GSK-3β-rich regions, including amygdala, cerebellum, and hippocampus. Also, it could be specifically blocked using the corresponding standard compounds With these results, this work sets the basis for further development of novel 18F-labeled GSK-3β PET probes.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran(SMILESS: BrCCOC1CCCCO1,cas:17739-45-6) is researched.Recommanded Product: 1970-40-7. The article 《Oxidative Addition to Palladium(0) Made Easy through Photoexcited-State Metal Catalysis: Experiment and Computation》 in relation to this compound, is published in Angewandte Chemie, International Edition. Let’s take a look at the latest research on this compound (cas:17739-45-6).

Visible-light induced, palladium catalyzed alkylations of α,β-unsaturated acids with unactivated alkyl bromides are described. A variety of primary, secondary, and tertiary alkyl bromides are activated by the photoexcited palladium metal catalyst to provide a series of olefins at room temperature under mild reaction conditions. Mechanistic studies and d. functional theory (DFT) studies suggest that a photoinduced inner-sphere mechanism is operative in which a barrierless, single-electron transfer oxidative addition of the alkyl halide to Pd0 is key for the efficient transformation.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (R)-(-)-3-Fluoropyrrolidine Hydrochloride( cas:136725-55-8 ) is researched.Quality Control of (R)-(-)-3-Fluoropyrrolidine Hydrochloride.Campbell, Nancy H.; Smith, Daniel L.; Reszka, Anthony P.; Neidle, Stephen; O’Hagan, David published the article 《Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA》 about this compound( cas:136725-55-8 ) in Organic & Biomolecular Chemistry. Keywords: fluorine medicinal chem fluorination pyrrolidine acridine G quadruplex DNA. Let’s learn more about this compound (cas:136725-55-8).

Comparative X-ray structure studies reveal that C-F bond incorporation into the peripheral pyrrolidine moieties of the G-quadruplex DNA binding ligand BSU6039 leads to a distinct pyrrolidine ring conformation, relative to the non-fluorinated analog, and with a different binding mode involving reversal of the pyrrolidinium N+-H orientation.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Lorton, Charlotte; Voituriez, Arnaud published the article 《Phosphine-Promoted Synthesis of 9H-Pyrrolo[1,2-a]indole Derivatives via an γ-Umpolung Addition/Intramolecular Wittig Reaction》. Keywords: pyrroloindole synthesis phoshine promoted Michael intramol Wittig indolecarbaldehyde allenoate.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Safety of 5-Methoxy-1H-indole-2-carbaldehyde. 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:21778-81-4) here.

The synthesis of substituted 9H-pyrrolo[1,2-a]indole products from 1H-indole-2-carbaldehydes and allenoates is described, using a phosphine-promoted Michael addition/intramol. Wittig reaction. This halide- and base-free methodol. provides an efficient access to different tricyclic nitrogen-containing heterocycles (18 examples, 32-88% isolated yields).

There is still a lot of research devoted to this compound(SMILES：O=CC(N1)=CC2=C1C=CC(OC)=C2)Safety of 5-Methoxy-1H-indole-2-carbaldehyde, and with the development of science, more effects of this compound(21778-81-4) can be discovered.

Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Helicates with Ether-Substituted Catechol Esters as Ligands, the main research direction is titanium lithium catechol complex preparation; crystal structure titanium lithium catechol complex.Synthetic Route of C7H13BrO2.

Mono- or biscatechol esters with ether-type substituents or spacers form either triple lithium bridged dimeric helicates or triple stranded helicates with the ability to bind three lithium cations in their interior. Hierarchical helicates with ether or thioether substituents show in solution a monomer-dimer equilibrium which is independent of the heteroatom in the ester substituent. However, dimerization constants are significantly lower than for corresponding alkyl derivatives Dinuclear helicates with oligoether spacers are well obtained in the presence of lithium cations. Upon removal of the cations the helicates expand and successive addition of LiCl results in compression again.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem