1020722-10-4

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 1236255-71-2 C₂₉H₁₈Br₂N₆O 
• 1236255-72-3 C₂₉H₁₉BrN₆O 
• 1236255-70-1 C₂₉H₁₈BrClN₆O 
• 1236255-69-8 C₂₉H₁₈Br₂N₆O 
• 1292766-38-1 3-cyano-2-(5-bromo-1H-indol-3-yl)-4-(2-naphthyl)-6-(4-ethylphenyl)pyridine 
• 1292770-01-4 2-(5-bromoindol-3-yl)-3-cyano-4-(4-diphenylaminophenyl)-6-phenylpyridine 
• 1354630-77-5 8-(6-(5-bromo-1H-indol-3-yl)-5-cyano-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)-1-naphthoic acid 
• 121963-43-7 1-(5-bromo-1-(phenylsulfonyl)-1H-indol-3-yl)ethanone 
• 19620-90-7 1-(5-bromo-1H-indol-3-yl)ethan-1-one 
• 1384512-37-1 C₂₄H₁₃BrClN₃ 
• 1384512-30-4 C₂₄H₁₄BrN₃ 
• 1400570-68-4 C₂₈H₁₈BrClN₂O₂ 
• 1400570-69-5 C₂₈H₁₇BrCl₂N₂O₂ 
• 1454306-01-4 2-amino-6-(5-bromo-1H-indol-3-yl)-4-(4-nitrophenyl)-4H-pyran-3,5-dicarbonitrile 

Relevant academic research and scientific papers

Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.

Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents

In the present investigation, synthesis of a series of extended conjugated δ-chloro-α-cyano substituted indolyl chalcones (5a–p) was accomplished by reacting 3-cyanoacetylindole 2 with 3-chloro-3-phenyl-propenal 4 in the presence of piperidine. The struct

Synthesis of indole-cycloalkyl[b]pyridine hybrids via a four-component six-step tandem process

The one-pot four-component reaction of 3-(1H-indol-3-yl)-3-oxopropanenitriles, aromatic aldehydes, cycloalkanones and ammonium acetate occurred via a six-step tandem Knoevenagel condensation-nucleophilic addition to carbonyl-Michael addition-N-cyclization-elimination-air oxidation sequence to afford structurally intriguing indole-cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles in excellent yields.

Base-Promoted Tandem Cyclization for the Synthesis of Polyfunctional 2-Hydroxy-2,3-dihydrofurans from Arylglyoxal Monohydrates and 3-(1 H -Indol-3-yl)-3-oxopropanenitrile

An efficient base-promoted tandem cyclization for the synthesis of polyfunctional 2-hydroxy-2,3-dihydrofurans from arylglyoxal monohydrates and 3-(1 H -indol-3-yl)-3-oxopropanenitrile has been established. The investigation of the mechanism suggested that this reaction proceeds through a Knoevenagel condensation-Michael addition-oxidation-cyclization sequence. This method demonstrates the compatibility with a wide range of functional groups to produce the 2-hydroxy-2,3-dihydrofuran scaffolds in good to excellent yields in one pot.

Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents

A series of novel α-cyano substituted indolyl bis-chalcones (3a-l) has been synthesized and evaluated for their in vitro antitumor activity against the human breast cancer MCF7 (estrogen receptor-positive) and normal Vero cell lines using sulforhodamine B (SRB) assay method. Compounds 3a, 3c and 3d showed potent activity (GI50 = 11.7, 15.3 and 17.9 μM respectively) against the human breast cancer MCF7 cell line, which was almost as good as that of adriamycin (GI50 = 0.1 μM) whereas, screening against the normal Vero Monkey cell line showed moderate selectivity. Furthermore, all the synthesized compounds screened for their antioxidant potential against DPPH, NO, SOR, and H2O2 radicals. Most of the bis-chalcones exhibited significant DPPH (51.09-12.72 %) and NO (64.11-34.43 %) radical scavenging activity and modest activity against SOR (88.08-43.14 %) and H2O2 (80.13-56.0 %) radicals compared to the reference standard ascorbic acid (40.78 %, 42.63 %, 87.05 %, and 79.42 % respectively). Current study provides impetus for the development of highly potent indolyl bis-chalcone derivatives as anticancer leads.

Rh(iii)-Catalyzed dual C-H functionalization of 3-(1: H -indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds toward polysubstituted carbazoles

A rhodium-catalyzed annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds has been developed, leading to a series of polysubstituted carbazoles in moderate to good yields. This procedure proceeded with formal Rh(iii)-catalyzed (4 + 2) cycloaddition, with the functionalization of 2-C-H bonds of indole in a step-economical procedure. Additionally, this reaction could also be conducted under acidic conditions when diazo compounds were employed as the reaction partners, which was a complement to the annulation of sulfoxonium ylides under weak basic conditions.

A facile cyanoacetylation of indoles with cyanocetic acid and propionic anhydride

A facile method for the synthesis of 3-cyanoacetyl indole derivatives mediated by propionic anhydride is described. These 3-cyanoacetylindole derivatives have been used in a starting material for the syntheses of various new compounds like (E)-2- ((1H-ind

Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles

The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles 3. Further reaction with aminoguanidine yielded 5'-cyanomeridianin analogues 4. The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative 8. Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate 3a with hydroxylamine hydrochloride in basic medium afforded (5-amino-isoxazol-4- yl)-(1H-indol-3-yl)-methanone 5 and the acrylic acid derivative 6 after a short or a long heating, respectively. Unequivocal structural elucidation of the latter compound was achieved from single-crystal X-ray diffraction studies. ARKAT-USA, Inc.

Novel and simple methodology for the synthesis of 3-acetylindoles and their N-alkyl derivatives using TBAB as phase transfer catalyst

Using 5% aq. NaOH, a simple method for the transformation of 3-cyanoacetylindoles 2(a-e) into 3-acetylindoles 3 (a-e), in good yields, is reported. Tetrabutylammoniumbromide (TBAB) is found to be an efficient phase transfer catalyst for the synthesis of N-alkyl derivatives 5(a-t) of 3-acetylindoles 3(a-e) giving products in excellent yields. 2 (a-e) were themselves obtained from simple indoles 1 (a-e) by reaction with cyano acetic acid in the presence of propionic anhydride at 100 °C for 5-10 min. Partial hydrolysis of 2 (a-e) under hot acidic conditions yielded the corresponding carboxamides α-(3-indolecarboxoyl)acetamides 4(a-e). Which could be readily transformed into the respective 3(a-e) by refluxing with 5% aq. NaOH for 2-2.5 h.