Category: 21778-81-4

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

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

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).

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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 Rapid and selective access to three distinct sets of indole-based heterocycles from a single set of Ugi-adducts under microwave heating. Author is Zhang, Lei; Zhao, Fei; Zheng, Mingyue; Zhai, Yun; Liu, Hong.

Three distinct sets of indole-based heterocycles, e.g. I, II and III, were rapidly and selectively synthesized from the same set of Ugi-adducts, e.g. IV, under microwave heating in a reaction-condition-controlled manner. Notably, an unprecedented metal-free intramol. sp3-hybridized C-H arylation using only cesium carbonate was discovered.

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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.Liou, Jing-Ping; Wu, Zi-Yi; Kuo, Ching-Chuan; Chang, Chi-Yen; Lu, Pei-Yi; Chen, Chi-Ming; Hsieh, Hsing-Pang; Chang, Jang-Yang researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Electric Literature of C10H9NO2.They published the article 《Discovery of 4-Amino and 4-Hydroxy-1-aroylindoles as Potent Tubulin Polymerization Inhibitors》 about this compound( cas:21778-81-4 ) in Journal of Medicinal Chemistry. Keywords: indole trimethoxybenzoyl chloride aroylation; trimethoxybenzoic anhydride indole acylation; indoline trimethoxybenzoyl chloride aroylation; tetrahydroquinoline trimethoxybenzoyl chloride acylation; aroylindole derivative preparation antitubulin anticancer activity; aroylindoline derivative preparation antitubulin anticancer activity; aroyltetrahydroquinoline derivative preparation antitubulin anticancer activity. We’ll tell you more about this compound (cas:21778-81-4).

1-Aroylindoline, 1-aroyl-1,2,3,4-tetrahydroquinoline, and 1-aroylindole derivatives, e.g., I and II, were synthesized and evaluated for anticancer activity. The 4-amino and 4-hydroxy-1-aroylindoles I and II, with IC50 of 0.9 and 0.6 μM, resp., exhibited antitubulin activity superior or comparable to that of colchicine and combretastatin A-4. They also showed antiproliferative activity with IC50 of 0.3-5.4 nM in a set of human cancer cell lines.

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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.HPLC of Formula: 21778-81-4.Zhang, Lei; Zhao, Fei; Zheng, Mingyue; Zhai, Yun; Wang, Jiang; Liu, Hong published the article 《Selective Synthesis of 5,6-Dihydroindolo-[1,2-a]quinoxalines and 6,7-Dihydroindolo-[2,3-c]quinolines by Orthogonal Copper and Palladium Catalysis》 about this compound( cas:21778-81-4 ) in European Journal of Organic Chemistry. Keywords: dihydroindoloquinoxaline dihydroindoloquinoline preparation copper palladium catalyst; Ugi four component reaction. Let’s learn more about this compound (cas:21778-81-4).

In combination with the Ugi four-component reaction, two important indole-fused heterocycles were prepared in two steps from readily accessible starting materials. From the same set of Ugi adducts 5, 5,6-dihydroindolo[1,2-a]quinoxalines were rapidly generated in excellent yields by a copper-catalyzed N-H arylation pathway, whereas 6,7-dihydroindolo[2,3-c]quinolones were obtained by palladium-catalyzed C-H arylations in good yields without the protection of the indole N1 moiety. Microwave heating was used to accelerate these intramol. C-N and C-C bond-forming reactions performed under controlled reaction conditions.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Atwell, Graham J.; Milbank, Jared J. B.; Wilson, William R.; Hogg, Alison; Denny, William A. published the article 《5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles: Relationships between Structure and Cytotoxicity for Analogues Bearing Different DNA Minor Groove Binding Subunits》. Keywords: chloromethyl benzindole preparation cytotoxicity structure.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Name: 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.

A series of 5-amino-seco-CBI compounds, designed for use as effectors for prodrugs, were prepared to study structure-activity relationships for the cytotoxicity of side chain analogs. Compounds were prepared by coupling 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benz[e]indole to appropriate carboxylic acids, followed by nitro group reduction, or by coupling suitable 5-amino-protected indolines to α,β-unsaturated acids, followed by deblocking. These AT-specific DNA alkylating agents were evaluated for cytotoxicity in a series of tumor cell lines (AA8, UV4, EMT6, SKOV3). For those analogs bearing an indolecarbonyl side chain, the 5′-methoxy derivative was the most cytotoxic (IC50 1.3 nM in AA8 cells, 4 h exposure), comparable to that of the parent CBI-TMI (5′,6′,7′-trimethoxyindole) derivative (IC50 0.46 nM in the above assay). A subset of solubilized derivatives bearing O(CH2)2NMe2 substituents were about 10-fold less potent. For compounds containing an acryloyl linker in the side chain, the 4′-methoxycinnamoyl derivative proved the most cytotoxic (IC50 0.09 nM in the above assay). A number of these 5-amino-seco-CBI-TMI analogs (including the solubilized compounds) are of interest both as cytotoxins and as components of amine-based prodrugs designed for tumor-specific activation.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthetic Route of C10H9NO2. 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 Three-Step One-Pot Synthesis of 1,4-Dihydropyrazolo[4,3-b|indoles Using Copper Catalysis. Author is Liu, Hailong; Zhang, Lei; Zhao, Fei; Liu, Hong.

A convenient three-step one-pot copper-catalyzed method has been developed for the preparation of pyrazolo[4,3-b]indoles, new indole-based compounds with potential biol. activity. Treatment of various hydrazines, including alkyl hydrazines, with indole-2-carbaldehydes generated the corresponding products in moderate to good yields without protection of the indole N-1 moiety. In addition, LiOH was used as a base in the copper-catalyzed coupling reaction. Microwave heating was used to accelerate the iodination of indoles and the C-N bond formation.

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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 Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes, the main research direction is formylpyrrole aminoiodoarene copper sparteine annulation; formylindole aminoiodoarene copper annulation sparteine; formylimidazole aminoiodoarene copper annulation sparteine; formylbenzimidazole aminoiodoarene copper annulation sparteine; formylpyrazole aminoiodoarene copper annulation sparteine; fused heterocyclic nitrogen containing preparation; annulation catalyst copper sparteine.Product Details of 21778-81-4.

In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Tsotinis, Andrew; Afroudakis, Pandelis A.; Davidson, Kathryn; Prashar, Anjali; Sugden, David published the article 《Design, Synthesis, and Melatoninergic Activity of New Azido- and Isothiocyanato-Substituted Indoles》. Keywords: indole azido isothiocyanato preparation melatoninergic.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Electric Literature of C10H9NO2. 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.

To develop irreversibly binding ligands for the melatonin receptor(s) as tools for tracing the primary melatonin binding site, novel melatoninergic azido- and isothiocyanato-substituted indoles were designed and synthesized. All active compounds were partial agonists or antagonists in the Xenopus melanophore assay, the most potent being 3-(2-azidoethyl)-5-methoxyindole and 3-(2-isothiocyanatoethyl)-5-methoxyindole.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem