Heterocyclic Building Blocks-Pyridazine

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 Base-dependent formation of cis and trans olefins and their application in the synthesis of 5-oxo-ETE receptor antagonists, published in 2014-08-01, which mentions a compound: 21778-81-4, mainly applied to stereoselective Wittig indolecarboxaldehyde oxo ETE receptor antagonist preparation; base dependent Wittig stereochem oxo ETE receptor antagonist preparation; 5-Oxo-ETE; Antagonist; Indolecarboxaldehyde; KHMDS; LiHMDS; Wittig reaction, Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde.

5-Oxo-ETE is the most potent eosinophil chemoattractant among lipid mediators. We have developed two 5-oxo-ETE receptor antagonists. In the course of the work, we have developed a procedure to selectively introduce a cis and trans double bond in an alkyl side chain. Reacting indolecarboxaldehydes with alkyl ylides using the Li base affords the trans olefins, whereas using the K base yields the cis olefins.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Safety of 2-(2-Bromoethoxy)tetrahydro-2H-pyran. 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. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Tuning the Mechanical Properties of a Polymer Semiconductor by Modulating Hydrogen Bonding Interactions.

Conjugation breakers (CBs) with different H-bonding chemistries and linker flexibilities are designed and incorporated into a diketopyrrolopyrrole (DPP)-based conjugated polymer backbone. The effects of H-bonding interactions on polymer semiconductor morphol., mech. properties, and elec. performance are systematically investigated. We observe that CBs with an H-bonding self-association constant >0.7 or a denser packing tendency are able to induce higher polymer chain aggregation and crystallinity in as-casted thin films, resulting in a higher modulus and crack on-set strain. Addnl., the rDoC (relative degree of crystallinity) of the stretched thin film with the highest crack on-set strain only suffers a small decrease, suggesting the main energy dissipation mechanism is the breakage of H-bonding interactions. By contrast, other less stretchable polymer films dissipate strain energy through the breakage of crystalline domains, indicated by a drastic decrease in rDoC. Furthermore, we evaluate their elec. performances under mech. strain in fully stretchable field-effect transistors. The polymer with the highest crack on-set strain has the least degradation in mobility as a function of strain. Overall, these observations suggest that we can aptly tune the mech. properties of a polymer semiconductor by modulating intermol. interactions, such as H-bonding chem. and linker flexibility. Such understanding provides mol. design guidelines for future stretchable semiconductors.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 21778-81-4, is researched, Molecular C10H9NO2, about Organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization: sustainable access to indole-2,3-fused diazocanes, the main research direction is formylindole aminoaniline triflic acid aldimine condensation Mannich cyclization tandem; benzodiazocino indole preparation green chem.Electric Literature of C10H9NO2.

An unprecedented organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization of indole-2-carbaldehydes with o-aminoanilines was developed to assemble polycyclic indole-2,3-fused diazocanes in one step. This novel methodol. featured high step- and atom-economy, was redox-neutral and metal-free, and occurred at room temperature It opened a new window for the application of hydride transfer chem. in constructing medium-sized ring structures.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Name: 5-Methoxy-1H-indole-2-carbaldehyde. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Asymmetric organocatalytic N-alkylation of indole-2-carbaldehydes with α,β-unsaturated aldehydes: one-pot synthesis of chiral pyrrolo[1,2-a]indole-2-carbaldehydes. Author is Hong, Liang; Sun, Wangsheng; Liu, Chunxia; Wang, Lei; Wang, Rui.

Diphenylprolinol trimethylsilyl ether-catalyzed asym. aza-Michael addition/aldol addition of indole-2-carboxaldehyde with unsaturated aldehydes is described. A series of chiral pyrrolo[1,2-a]indole-2-carbaldehydes were obtained in good yields with excellent stereoselectivities.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Reference of 5-Methoxy-1H-indole-2-carbaldehyde. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Catalysis based on C-I···π halogen bonds: electrophilic activation of 2-alkenylindoles by cationic halogen-bond donors for [4+2] cycloadditions. Author is Kuwano, Satoru; Suzuki, Takumi; Yamanaka, Masahiro; Tsutsumi, Ryosuke; Arai, Takayoshi.

Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles catalyzed by cationic halogen-bond donors were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Exptl. and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C-I···π halogen bonds.

In addition to the literature in the link below, there is a lot of literature about this compound(5-Methoxy-1H-indole-2-carbaldehyde)Reference of 5-Methoxy-1H-indole-2-carbaldehyde, illustrating the importance and wide applicability of this compound(21778-81-4).

Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Recommanded Product: 136725-55-8. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (R)-(-)-3-Fluoropyrrolidine Hydrochloride, is researched, Molecular C4H9ClFN, CAS is 136725-55-8, about Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors. Author is Caldwell, Charles G.; Chen, Ping; He, Jiafang; Parmee, Emma R.; Leiting, Barbara; Marsilio, Frank; Patel, Reshma A.; Wu, Joseph K.; Eiermann, George J.; Petrov, Aleksandr; He, Huaibing; Lyons, Kathryn A.; Thornberry, Nancy A.; Weber, Ann E..

Amides derived from fluorinated pyrrolidines and 4-substituted cyclohexylglycine analogs have been prepared and evaluated as inhibitors of dipeptidyl dipeptidase IV (DP-IV). Analogs which incorporated (S)-3-fluoropyrrolidine showed good selectivity for DP-IV over quiescent cell proline dipeptidase (QPP). Amide I had good pharmacokinetic properties and was orally active in an oral glucose tolerance test in lean mice.

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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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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

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

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