40747-12-4

Upstream product

• 703-80-0 3-acetylindole 
• 120-72-9 indole 

Downstream Products

• 51030-59-2 N-(1H-indol-3-yl)acetamide 

Relevant academic research and scientific papers

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains

Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.

Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate

A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.

Synthesis, biological evaluation, and structure-activity relationships of N -benzoyl-2-hydroxybenzamides as agents active against P. falciparum (K1 strain), trypanosomes, and leishmania

In our efforts to identify novel chemical scaffolds for the development of new antiprotozoal drugs, a compound library was screened against Toxoplasma gondii tachyzoites with activity discovered for N-(4-ethylbenzoyl)-2- hydroxybenzamide 1a against T. gon

An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)

An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.

Diels-Alder Reactions of (1H-Indol-3-yl)-enacetamides and -endiacetamides: A Selective Access to Acetylamino-Functionalized Annelated Indoles and Carbazoles

Diels-Alder reactions of the (1H-indol-3-yl)-enacetamides and -endiacetamides 1a - d with some carbodienophiles and 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione give rise to the novel amino-functionalized carbazoles 4 - 6 and 8 (Scheme 3).Ethenetetracarbonitrile reacts with 1b to furnish the Michael-type adduct 7 (Scheme 3).Structural aspects of the starting materials 1, which exhibit above all 3-vinyl-1H-indole reactivity, are discussed with regard to the prediction of a Diels-Alder process.

Indoles and Indole Alkaloids, XXI. - Preparation of 4-(Acetylamino)-1,2,3,9a-tetrahydrocarbazole Derivatives by Cycloadditions of 3-Indolyl-enimides and -enamides

Treatment of the oximes of the 3-acetylindoles 1 and 5 with acetic anhydride in pyridine results in the formation of the enimides 2 and 7, which slowly undergo cycloadditions with acrolein and derivatives of acrylic acid to form 3 and 10, respectively.Com

STRUCTURE OF 3-ACYLINDOLE OXIMES

On the basis of an analysis of the PMR spectra of 3-acylindole oximes it is shown that these compounds, like 3-acylindoles, have an s-trans conformation and exist primarily in the form of syn isomers.The structure of 1-methyl-3-acetylindole s-trans-syn-ox