Category: 21778-81-4

Hao, Yanke; Zhou, Pan; Niu, Kaikai; Song, Hongjian; Liu, Yuxiu; Zhang, Jingjing; Wang, Qingmin published the article 《Synthesis of Indole- and Pyrrole-Fused Seven-Membered Nitrogen Heterocycles via Acid-Base Switchable Cyclization Involving Cleavage of Amide C-N Bonds》. Keywords: tetrahydro diazepinoindolone sulfonyl preparation chemoselective; sulfonyl tetrahydroazepinoindolone preparation chemoselective; indolyl methyl sulfonyl acrylamide switchable heterocyclization acid base catalyst.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Application In Synthesis 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 method for synthesis of indole- and pyrrole-fused seven-membered nitrogen heterocycles I [R = H, Br; R1 = H; RR1 = -CH=CHCH=CH-, -CH=C(OMe)CH=CH-, -CH=CHC(Br)=CH-, etc.; R2 = H, Me, 3-(trifluoromethyl)phenyl, ethyloxidanyl; R3 = H, Me; R4 = Me, 4-methylphenyl, thiophen-2-yl, etc.], 2-tosyl-1,2,3,4-tetrahydro-5H-[1,5]diazocino[3,2,1-hi]indol-5-one and II (R5 = H, OMe; R6 = Me, 2-fluorophenyl, thiophen-2-yl, etc.) by means of acid-base switchable cyclization reactions have been reported. The reactions involved cleavage of amide C-N bonds, chemoselective N-1 or C-3 acylation, and 1,4-Michael addition This method could be used to construct two different kinds of seven-membered rings in one step from the same starting material without the need for a transition-metal catalyst.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, ACS Catalysis called Enantioselective Synthesis of Polycyclic Indole Derivatives Based on aza-Morita-Baylis-Hillman Reaction, Author is Gao, Yuning; Xu, Qin; Shi, Min, which mentions a compound: 21778-81-4, SMILESS is O=CC(N1)=CC2=C1C=CC(OC)=C2, Molecular C10H9NO2, Category: pyridazine.

A chiral phosphine-catalyzed asym. aza-Morita-Baylis-Hillman reaction between indole-derived sulfonyl imines and bis(3-chlorophenyl)methyl acrylate has been developed, giving the desired adducts in good yields and enantiomeric excess values along with the further transformations to polycyclic indoles such as dihydropyrido[1,2-a]indole and dihydropyrazino[1,2-a]indole skeleton.

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Pyridazine – Wikipedia,
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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 Discovery of 4-Amino and 4-Hydroxy-1-aroylindoles as Potent Tubulin Polymerization Inhibitors, published in 2008-07-24, which mentions a compound: 21778-81-4, mainly applied to 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, Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde.

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

Safety of 5-Methoxy-1H-indole-2-carbaldehyde. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Synthesis of carbazole derivatives. III. Synthesis of new pyrrolidino[3,4-c]carbazoles by intramolecular Michael addition. Author is Mahboobi, Sioavosh; Kuhr, Sabine; Koller, Markus.

The authors have reported on the synthesis of carbazoles by inter- and intramol. Michael addition Ellipticine derivatives are related to these compounds, and especially those with 9-methoxy- and 9-hydroxy substituents exhibit appreciable antitumor and antileukemic activity. Therefore, the authors have prepared the tetrahydrocarbazoles I (R1 = OMe, R2 = H; R1 = H, R2 = OMe), starting from N-benzyl-2-formyl-5-methoxyindole and N-benzyl-2-formyl-7-methoxyindole, resp.

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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 Coupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Stereocenters, the main research direction is alkene intramol hydroacylation enantioselective arylation nickel NHC catalyst; heterocyclic ketone chiral quaternary stereocenter stereoselective preparation.Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde.

We report a strategy that combines alkene hydroacylation and enantioselective α-(hetero)arylation reactions to form a wide variety of nitrogen-containing heterocyclic ketones bearing α-chiral quaternary stereogenic centers. Exo-selective, intramol. Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form α-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of N-allylindole- and N-allylpyrrole-2-carboxaldehydes form α-substituted five-membered heterocyclic ketones in up to 99% yield. The racemic five- and six-membered products of Ni- and NHC-catalyzed hydroacylation reactions are readily transformed into heterocyclic ketones containing an α-chiral quaternary stereogenic center by enantioselective Ni-catalyzed α-arylation and α-heteroarylation reactions. The chiral, nonracemic products formed through a combination of alkene hydroacylation and α-(hetero)arylation reactions are formed in moderate to high yields (44-99%) with excellent enantioselectivities (typically >95% ee). The identity of the precatalyst for Ni-catalyzed α-(hetero)arylation is dictated by the identity of the α-substituted heterocyclic ketone starting material. α-(Hetero)arylations of six-membered heterocyclic ketones occur at 65-85 °C in the presence of a catalyst generated in situ from Ni(COD)2 and (R)-BINAP or (R)-DIFLUORPHOS. α-(Hetero)arylation of five-membered heterocyclic ketones must be conducted at room temperature in the presence of an [((R)-BINAP)Ni(η2-NC-Ph)] precatalyst or a catalyst generated in situ from Ni(COD)2, (R)-DIFLUORPHOS, and benzonitrile.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Application of 21778-81-4. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. 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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Methoxy-1H-indole-2-carbaldehyde(SMILESS: O=CC(N1)=CC2=C1C=CC(OC)=C2,cas:21778-81-4) is researched.Application of 21778-81-4. The article 《Synthetic studies on mitomycins. Synthesis of aziridinopyrrolo[1,2-a]indoles》 in relation to this compound, is published in Tetrahedron Letters. Let’s take a look at the latest research on this compound (cas:21778-81-4).

Conversion of the nitro compounds 2,4,5-Me(R1O)R2C6H2NO2 (R1, R2 = Me, H; Me, Me; PhCH2O, H; PhCH2O, Me) by a modified Reissert indole synthesis gave the esters I (R3 = CO2Et), m. 155-6, – , – , 141-2°, resp., reduced by LiAlH4 to the alcs. I (R3 = CH2OH), m. 83.5-5.0, 139-40, 103-4, 100-3°, resp., oxidized in turn by KMnO4 in Me2CO with poor yields (10-20%) or with yields up to 90% by CrO3-C5H5N of the corresponding aldehydes I (R3 = CHO), m. 136-7, 172-3, 178-9, 172-5°, resp. The aldehydes treated with NaH and H2C:CHPPh3Br in tetrahydrofuran (THF) gave 80-8% yields of 9H-pyrrolo[1,2-a]indoles (II) (R1, R2 = Me, H; PhCH2O, H; PhCH2O, Me), m. 80-1, 88-9, 88-9°, resp., with structures supported by uv and N.M.R. spectra. Acylation of II with KOCMe3 and Me2CO3 afforded 60-80% 3H-pyrrolo-[1,2-a]indoles (III) (R4 = OMe), m. 121-3, 122-3, 139-41°, resp. Similarly acylation with HCO2Et gave III (R4 = H; R1, R2 = Me, H; PhCH2O, Me), m. 135-41 (decomposition), and 138-42°, with structures supported by ir, uv, and N.M.R. spectra. Functionalization of the vinylic double bond of III for attachment of the aziridine moiety was achieved by iodine-azide addition giving 74-5% yields of iodo-azides (IV, R1, R2 = Me, H; PhCH2O, Me), m. 93.8-4.5, and 171-9°, ir, uv, and N.M.R. spectral data given. Catalytic hydrogenation of IV over Pd-C in MeOH containing HCl gave 60-90% yields of the corresponding iodo-amine hydrochlorides, m. >300, >300°, yielding the expected iodoamines, m. indefinite, 135-41° (decomposition), resp., ir bands (Nujol) given. Protection of the amine group with ClCO2Me furnished the iodo carbamates (V) (R5 = H; R1, R2 = Me, H; PhCH2O, Me) (VI, VII), m. 160-2 and 183-4°, resp. Cyclization with NaOMe in (MeOCH2)2 or THF gave VIII (R5 = H; R1 = Me, R2 = H), m. 210.5-14.5°, with structure confirmed by spectroscopic data, and VIII (R5 = H, R1 = PhCH2O, R2 = Me), m. 219.5-21.5°. Nitration of VI and VII gave the 8-nitro derivatives V (R5 = NO2, R1, R2 = Me, H; PhCH2O, Me), m. indefinite and 192-9°, resp. The location of the NO2 group was elucidated by N.M.R. spectral anal. The ring closure of the 8-nitro derivatives similarly gave the corresponding aziridines, VIII (R5 = NO2; R1, R2 = Me, H; PhCH2O, Me), m. 242-6, and 232-3.5°.

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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: 5-Methoxy-1H-indole-2-carbaldehyde(SMILESS: O=CC(N1)=CC2=C1C=CC(OC)=C2,cas:21778-81-4) is researched.Product Details of 21778-81-4. The article 《Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones》 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:21778-81-4).

The aromatic nitrogen atoms of heteroarylaldehydes were activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products I [R1 = H, 8′-Br, 7′-Cl, etc.; R2 = H, 4-Br, 5-Cl, etc.; R3 = Me, Bn, Trt], II [R1 = H, 8-Br, 7-F, etc.; R2 = H, 3-Me, 4-Cl, etc.; R3 = Me, Et, Ph, Bn, CHPh2] and III [R1 = H, 6;t-Bu, 7’Cl, etc.; R2 = H, 4-Cl, 5-Me, etc.] were afforded in good to excellent yields and optical purities. Reaction involved the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibited excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichems. for plant protection.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Nishiyama, Takashi; Hatae, Noriyuki; Yoshimura, Teruki; Takaki, Sawa; Abe, Takumi; Ishikura, Minoru; Hibino, Satoshi; Choshi, Tominari published the article 《Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells》. Keywords: carbazolequinone preparation antiproliferative human; indole allyl alc tandem ring closing metathesis dehydrogenation; Antiproliferative activity; Carbazole-1,4-quinone; Koeniginequinone A; Koeniginequinone B.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Reference 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.

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R1 = R2 = H, CH3; R3 = H, 6-OCH3, 5,6-(OCH3)2, 7-CH3, 6-NO2, etc.; R4 = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

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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 Rapid Generation of Privileged Substructure-Based Compound Libraries with Structural Diversity and Drug-Likeness, the main research direction is indolecarboxaldehyde amine carboxylic acid isonitrile Ugi intramol arylation cyclization; heterocyclic compound library preparation structural diversity drug likeness.SDS of cas: 21778-81-4.

A library of privileged-substructure-based, heterocyclic compounds was constructed by a sequence of Ugi four-component reactions incorporating the indole motif and microwave-assisted cyclizations in branched pathways. Cheminformatic anal. confirmed that the library exhibited a high degree of structural diversity and good drug-likeness.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem