65287-74-3

Usage

Chemical structure

A ketone derivative containing a chloro-substituted indole ring

Pharmaceutical industry

As an intermediate for the production of various drugs

Organic synthesis

As a building block for the synthesis of more complex chemical compounds

Research applications

Study of indole-based compounds and their potential biological activities

Role in industry

Crucial in the development of new and advanced chemical compounds for various industries

Upstream product

• 59-48-3 2-oxoindole 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 172869-90-8 N-benzyl-2-chloro-3-acetyl-indole 
• 1352632-34-8 C₂₀H₁₇Cl₂NO 
• 1352632-32-6 C₂₁H₂₀ClNO₂ 
• 1185994-28-8 3-methyl-1-phenyl-1,8-dihydropyrazolo[3,4-b]indole 
• 1311380-64-9 1-(2-chloro-1-(5-phenylpent-4-ynyl)indol-3-yl)ethanone 
• 1311380-68-3 C₂₂H₂₀ClNO 
• 1311380-67-2 C₂₁H₁₇Cl₂NO 
• 1311380-66-1 C₂₂H₂₀ClNO₂ 
• 1311380-65-0 C₂₂H₂₀ClNO 
• 136093-84-0 1-methyl-2-phenylamino-3-(1-phenyliminoethylene)indole 
• 213591-09-4 1-{1-(methoxymethyl)-2-[(triphenylphosphoranylidene)amino]indol-3-yl}ethanone 

Relevant academic research and scientific papers

Ligand- and catalyst-free intramolecular C-S bond formation: Direct access to indalothiochromen- 4-ones

An efficient ligand- and catalyst-free intramolecular S-arylation leading to the direct synthesis of indalothiochromen-4-ones from simple dithioesters under mild conditions has been developed. This method is particularly noteworthy given its experimental

Photoinduced chlorine atom-transfer cyclization/photohydrolysis of 3-acyl-2-chloro-N-(ω-phenylalkynyl)pyrroles: A one-pot synthesis of benzoyl-substituted fused pyrroles

A one-pot synthesis of benzoyl-substituted fused pyrroles or indoles in moderate to high yields has been achieved by the photocyclization/ photohydrolysis reactions of N-(ω-phenylalkynyl)-2-chloropyrrole-3- carbaldehydes or 3-acyl-N-(ω-phenylbutynyl)-2-haloindoles in wet acetone. The formation of all these products could be inferred by a two-step reactions, namely, photoinduced chlorine atom-transfer cyclization and subsequent photohydrolysis.

Photoinduced cyclization of 3-acyl-2-halo-1-[(ω-phenylethynyl)alkyl] indoles to azaheterocyclo[1,2,3- lm ]-fused benzo[ c ]carbazoles

A one-pot synthesis of azaheterocyclo[1,2,3-lm]-fused benzo[c]carbazoles (2 and 3) has been developed by photocyclization of 3-acyl-2-halo-1-[(ω- phenylethynyl)alkyl] indoles (1) in good to excellent yields. All products are formed from 1 via two sequential photocyclization reactions. Two products, 9-chloro-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2-h) and 7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (3-h), are produced in the photocyclization of 2-halo-1-[(ω-phenylethynyl)alkyl]indole-3- carbaldehydes (1-h). In contrast, only products 2-h are produced in the photocyclization of 3-acetyl-2-chloro-1-[(ω-phenylethynyl)alkyl]indole-3- carbaldehydes (1o - t). The 9-H in 3-h (n = 2) does originate from the formyl group in 1-h via 1,5-hydrogen shift. The structures of three new products, 9-bromo-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2b), 9-chloro-10-methyl-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (3h) and 12-chloro-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2w), have been corroborated by single-crystal X-ray structural analyses.

One-pot synthesis of fused benzo[c]carbazoles by photochemical intramolecular annulation of 3-acyl-2-haloindoles with tethered styrenes

An efficient procedure for the synthesis of fused benzo[c]carbazoles has been achieved in moderate to high yields by the one-pot photochemical annulation of 3-acyl-2-haloindoles with tethered styrenes by photoinduced electron-transfer coupling, electrocyclic reactions, and deacylative aromatization in the presence of pyridine. Fused furo[2,3-c]carbazoles were also synthesized under the same conditions. 5,6-Dihydrobenzo[c]pyrrolo[1,2,3-lm] carbazoles were oxidized by DDQ to afford aromatic benzo[c]pyrrolo[1,2,3-lm] carbazole products in moderate to high yields.

Photoinduced intramolecular addition of 3-acyl-2-haloindoles to alkenes

1,2-Fused indoles and pyrroles were prepared via an efficient intmolecular photoaddition reaction of 1-(ωalkenyl)-2 haloindole-3-carbaldehydes and 1-(ωalkenyl)-2 chloropyrrole-3-carbaldehydes. The presence of an acyl group was necessary for the photocycizntion reactions. The halogen-atom retained exo and endo cyclization prodects were generally prodeced with result similar to those of atom transfer cyclization reaction. in contrast, unsaturated cyclization prodects were obtained in the photoreactions of substrates having monthyl groups on vinyl group.

Intramolecular photochemical cross-coupling reactions of 3-acyl-2-haloindoles and 2-chloropyrrole-3-carbaldehydes with substituted benzenes

Highly efficient syntheses of indolo[2,1-a]isoquinolines, indolo[2,1-a][2]benzazepines, pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]benzazepines in excellent yields have been achieved by the intramolecular photochemical cross-coupling reactions of 3-acyl-2-halo-N- (ω-arylalkyl)indoles and 2-chloro-N-(ω-arylalkyl)pyrrole-3- carbaldehydes in acetone. A new heterocyclic ring system - pyrrolo[1,2-d][1,4] benzoxazepine - has also been constructed for the first time in this work by the photocyclization of 2-chloro-N-(2-phenoxyethyl)pyrrole-3-carbaldehyde.

ANTAGONISTS, THEIR PREPARATION AND USE

The present invention relates to therapeutically active non competitive antagonists, acting selectively at the metabotropic glutamate receptor. The novel compounds are useful in treating diseases in the central nervous system by modulating synaptic transmission via the metabotropic glutamate receptor.

THIENO[2,3-B-INDOLE DERIVATIVES AND THEIR USE FOR TREATING CENTRAL NERVOUS SYSTEM DISEASES RELATED TO THE METABOTROPIC GLUTAMATE RECEPTOR SYSTEM

The present invention relates to therapeutically active heterocyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system related to the metabotropic glutamate receptor system.

New 5H-1,2,4-triazino[5,6-b]indole and aminoindole derivatives. Synthesis and studies as inhibitors of blood platelet aggregation, anti-hypertensive agents and thromboxane synthetase inhibitors

This paper reports the synthesis of a series of 5H-1,2,4-triazino[5,6-b]indole 3 and 4, and aminoindole 12-23, derivatives, obtained from isatin 1 and from oxoindole 5, respectively. All the new compounds were studied as antihypertensive agents in spontaneously hypertensive rats (SHR), and as inhibitors of platelet aggregation in guinea pig whole blood, induced by arachidonic acid (AA), adenosin-5'-diphosphate (ADP) or collagen. The most active antiaggregating compounds were also studied as thromboxane A2 synthetase inhibitors.