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Synthesis of 3,1-Benzothiazines by Cyclisation of 2- Thioformylaminodiphenylacetylenes

2-Formylaminodiphenylacetylenes, obtained in excellent yield by Sonogashira coupling of (2-iodoaryl)formamides with phenylacetylene, were thionated with P4S10 in boiling THF to give 2-thioformylaminodiphenylacetylenes. These acetylenes were cyclised by DBU at ambient temperature to give (4Z)-4-benzylidene-4H-3,1-benzothiazines and small amounts of 2-phenylindoles. The structures of (4Z)-4-benzylidene-6,8-dichloro- 4H-3,1-benzothiazine and 3,5-dichloro-2-thioformylaminodiphenylacetylene were established by single crystal X-ray analysis.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N848 | ChemSpider

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Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

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Quinoxaline | C8H6N918 | ChemSpider

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Oxidative N-Heterocyclic Carbene Catalyzed Dearomatization of Indoles to Spirocyclic Indolenines with a Quaternary Carbon Stereocenter

An efficient method for the asymmetric intramolecular dearomatization of indoles by using oxidative N-heterocyclic carbene catalysis is demonstrated. Valuable optically active spirocyclic indolenines bearing an all-carbon quaternary stereocenter are obtained in excellent yields and with excellent enantioselectivity. The starting indoles are readily prepared and the reactions proceed through an intramolecular indole 3-acylation with an in situ generated acyl azolium intermediate to form a spirocyclic ketone moiety.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N833 | ChemSpider

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Kinetic resolution of indolines through reductive amination of aldehydes by chiral Br¡ãnsted acid

We have developed a highly efficient and practical strategy for the kinetic resolution of indoline derivatives, involving a chiral Br¡ãnsted acid-catalyzed iminium ion formation and asymmetric transfer hydrogenation cascade process. The kinetic resolution allows the synthesis of 2-substituted N-benzylindolines in good yields with moderate to excellent enantioselectivities.

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Regioselective Synthesis of 2-Substituted Indoles from Benzotriazoles and Alkynes by Photoinitiated Denitrogenation

Herein, we describe a photoinitiated and regioselective synthesis of 2-substituted indoles under mild reaction conditions. This biologically privileged scaffold was accessed in good yields from N-aroylbenzotriazoles, a quencher class previously identified using our mechanism-based luminescence screening, and terminal alkynes in the presence of a photocatalyst and blue light irradiation. This straightforward protocol displays a broad substrate scope and functional group tolerance. Furthermore, the mildness and robustness of the reaction were assessed by the application of an additive-based robustness screen. The determination of the reaction quantum yield and Stern-Volmer studies support the proposed photoinitiated radical chain mechanism.

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Quinoxaline – Wikipedia,
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Synthesis and antiserotonin activity of ethyl 5-O-(4-methylpiperazin-1-ylacetyl)-2-methylindole-3-carboxylates and 3-(4-methyl-1-piperazinylglyoxyl)indoles

Ethyl-5-O-chloroacetyl-2-methylindole-3-carboxylates (2a-e) have been synthesised by the reaction of ethyl 5-hydroxy-2-methylindole-3-carboxylates (1a-e) with chloroacetyl chloride in dry benzene containing triethylamine.These indoles (2a-e) on condensation with methylpiperazine in dry acetone in the presence of anhydrous K2CO3, afford ethyl 5-O-(4-methylpiperazin-1-ylacetyl)-2-methylindole-3-carboxylates (3a-e).Compounds 3a-e are converted into their oxalate derivatives (4a-e).Indole-3-glyoxyl chlorides (6a-e) have been prepared from appropriate indoles (5a-e) byreaction with oxalyl chloride in dry ether. these derivatives on condensation with methylpiperazine yield 3-(4-methyl-1-piperazinylglyoxylyl)indoles (7a-e) wich are converted into oxalate salts (8a-e).Compounds 4a-e and 8a-e have been screened for their antiserotonin activity.Only compound 4d is found to exhibit antiserotonin activity.

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A aromatic ring [a] carbazole and synthetic method of compound (by machine translation)

The invention discloses a aromatic ring and [a] Carbazole compound synthesis method, which belongs to the technical field of organic synthesis. The technical scheme of the present invention to point is: connected to the 2 – phenyl indole compound, 2 – (naphthalene – 1 – yl) indole compounds or 2 – (thiazole – 1 – yl) indole compounds with the diazo compounds are dissolved in the solvent, then adding catalyst and additive, for 100 – 140 C reaction, to respectively obtain benzo [a] Carbazole compound, naphtho [a] Carbazole compound or imidazo [a] Carbazole compound. The invention relates to 2 – substituted indole compound and diazo compounds as raw materials, through the one-pot Serial reaction, aromatic ring and directly [a] Carbazole compound, synthetic process operation is convenient, mild condition, substrate and wide range of application, is suitable for industrial production. (by machine translation)

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Anticonvulsant evaluation of clubbed indole-1,2,4-triazine derivatives: A synthetic approach

A series of thirty indole C-3 substituted 5-amino-6-(5-substituted-2- phenyl-1H-indol-1-yl)-4,5-dihydro-1,2,4-triazine-3(2H)-thione 5a-f, 6a-f, 7a-f, 8a-f and 9a-f were synthesized to explore prospective anticonvulsant agents. The derivative 1-(1-(5-amino-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)-5- fluoro-2-phenyl-1H-indol-3-yl)ethanone (6b) had significant activity in maximal electroshock test with minimal duration of limb extension (5.40 ¡À 0.61 s) and quantitative median dose of 7 mg/kg. In subcutaneous pentylenetetrazole screen 1-(5-amino-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)-5-fluoro-2- phenyl-1H-indole-3-sulfonamide (7b) increased the seizure latency to onset of clonus and was effective at a median dose of 35 mg/kg. An in vitro radioligand binding assay on sodium channel and gamma-amino butyric acid estimation was also performed on active compounds to perceive the mechanistic procedure responsible for it action.

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Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines

A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.

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Ruthenium-catalyzed tandem annulation/arylation for the synthesis of unsymmetrical bis(heteroaryl)methanes

A new Ru-catalyzed tandem furan annulation/arylation strategy has been developed to afford unsymmetrical bis(heteroaryl)methanes by a reaction between propargyl amines and indoles. A series of bis(heteroaryl)methanes containing furan and indole as well as indole and imidazopyridine moieties have been synthesized in high yields. The reaction possibly proceeds through furan annulation followed by nucleophilic addition of indole.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N903 | ChemSpider