61364-20-3

Basic information

• Product Name: 3,4-dihydro-Cyclopent[b]indol-1(2H)-one
• Synonyms: 3,4-dihydro-Cyclopent[b]indol-1(2H)-one;2,3-dihydrocyclopenta[b]indol-1(4H)-one;OC1171, 2,3-Dihydrocyclopenta[b]indol-1(4H)-one
• CAS NO: 61364-20-3
• Molecular Formula: C₁₁H₉NO
• Molecular Weight: 171.19526
• Mol File: 61364-20-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-dihydro-Cyclopent[b]indol-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydro-Cyclopent[b]indol-1(2H)-one(61364-20-3)
• EPA Substance Registry System: 3,4-dihydro-Cyclopent[b]indol-1(2H)-one(61364-20-3)

Safety Data

• Hazardous Substances Data: 61364-20-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-dihydro-Cyclopent[b]indol-1(2H)-one is used as a pharmaceutical compound for its neuroprotective, anti-inflammatory, and anticancer properties. Its potential pharmacological activities make it a promising candidate for the development of new drugs to treat various medical conditions.
Used in Drug Discovery and Development:
3,4-dihydro-Cyclopent[b]indol-1(2H)-one is used as a structural template in drug discovery and development due to its diverse biological activities and potential for further modification to enhance its therapeutic effects.
Used in Central Nervous System Research:
3,4-dihydro-Cyclopent[b]indol-1(2H)-one is used as a research compound in the study of the central nervous system, with potential applications as a therapeutic agent for various neurological and psychiatric conditions.

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Relevant articles and documents

Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes

On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann-Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately functionalized benzofurans, indoles, or phthalanes.

Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis

A highly efficient and flexible protocol for intramolecular annulation of exocyclic β-enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2-a]pyridines through a counter-anion-controlled free-radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C?C and C?N bond formation to give the desired products. The mechanistic insights suggest that the two competitive reactions involved in the system are guided by the nature of the counteranion, which determines the formation of the final products. A wide variety of carbazolones and imidazo[1,2-a]pyridine molecules have been prepared and isolated in good to excellent yields.

An easy access to carbazolones and 2,3-disubstituted indoles

Synthesis of carbazol-4-ones, 3,4-dihydrocyclopental-indol-1-one, and indole derivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones is demonstrated. The same protocol has been extended to access indolocarbazolone and indoloquinolone derivatives. Synthesis ofderivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation strategy is demonstrated. The starting materials were easily accessed from C-arylation of 1,3-diketones by o-nitroiodobenzenes. Copyright

1, 2, 3, 9-tetrahydro-4H-carbazol-4-one and 8, 9-dihydropyrido- [1, 2-a]indol-6(7H)-one from 1H-indole-2-butanoic acid

Efficient syntheses of the title ring systems have been developed from 1H-indole-2-butanoic acid, which was easily prepared from 2-fluoro-1- nitrobenzene in four steps. Heating 1H-indole-2-butanoic acid in toluene containing p-toluenesulfonic acid at 110°

TRICYCLIC CYTOPROTECTIVE COMPOUNDS

Compounds of formula (I): in which: X is a group of formula >CR1R2 or >SO2; Y is a group of formula >NH or >CR1R2; Z is a group of formula >C=O or >CH2 or a direct bond; R1 hydrogen and R2 is hydrogen, carboxy or hydroxy; or R1 and R2 together represent an oxo group, a methylenedioxy group or a hydroxyimino group; R3 is hydrogen or lower alkyl; R4 represents two hydrogen atoms, or an oxo or hydroxyimino group; R5 is hydrogen, lower alkyl or halogen; R6 is hydrogen, lower alkoxy or carboxy; R7 and R8 are each hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts and esters thereof can be used for the treatment or prophylaxis of acute or chronic neurodegenerative diseases or conditions such as Alzheimer’s Disease, Parkinson’s Disease, Huntington’s Chorea, Multiple Sclerosis or the sequelae to acute ischaemic events such as heart attack, stroke or head injury and for protection against ischaemic damage to tissues of peripheral organs.

Synthesis of Cyclopenta[b]indol-1-ones and Carbazol-4-ones from N-(2-Halophenyl)-Substituted Enaminones by Intramolecular Heck Reaction

An efficient synthetic route towards N-methylated or nonmethylated 3,4-dihydrocyclopent[b]indol-1(2H)-ones (3) and 1,2,3,9-tetrahydrocarbazol-4(4H)-one (10) was elaborated, based on Pd-catalyzed intramolecular Heck reaction. The chemoselectivity of the cyclization was studied in the case of the bi- and trifunctional substrates 12 and 17, respectively. In the latter case, depending on the catalyst, either the brominated indole 18 or the tetracyclic compound 19 were obtained by single and double Heck reaction, respectively.

Palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones. Formal total synthesis of murrayaquinone A

Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to 1,2-dihydro-4(3H)-carbazolones. The steps are an intermolecular Stille cross-coupling followed by a reductive N-heteroannulation. A formal total synthesis of murrayaquinone A, employing this sequence, is reported.

Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones

Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to carbazolones, an intermolecular Stille coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation. A number of functionalized 1,2-dihydro-4(3H)-carbazolones were prepared using this sequence.

Efficient photochemical synthesis of tricyclic keto-indoles

Tricyclic keto-indoles were synthesized by photocyclization of easily obtained enaminones in an electrocyclic photochemical reaction. The three methods reported were chosen according to the enaminone structure. The most general procedure using one-step synthesis was carried out in a benzene-methanol solution in the presence of sodium methylate. In the case of base sensitive substrates, the best method was photocyclization followed by oxidation. Besides, N-unsubstituted indoles with a five-membered ring were prepared by a photolysis reaction. All three methods are efficient and easy to perform.

ORGANIC NITROSONIUM SALTS. II. STABILITY STUDIES AND OXIDATIONS OF SOME INDOLE DERIVATIVES

The stabilities of various salts of the 2,2,6,6-tetramethylpiperidine-1-oxonium ion were studied. 2,2,6,6-Tetramethylpiperidine-1-oxonium tetrafluoroborate was shown to react with 1,2,3,4-tetrahydrocarbazole (1-H-2,3,4,9-tetrahydrocarbazole) to give, in the presence of water, 4-keto-1,2,3,4-tetrahydrocarbazole in good yield.Under the same conditions, cyclopentindole and cycloheptindole gave the corresponding keto derivatives.In the absence of water, the oxidation of tetrahydrocarbazole gave a mixture of dimers, probably derived from the Diels-Alder self condensation of 1-H-2,3-dihydrocarbazole.The condensation is reversible and, in acid, the dimer mixture gives a salt of 1-H-2,3-dihydrocarbazole which can be reduced with sodium borohydride to give back tetrahydrocarbazole.