Ultrasound assisted synthesis of N-aryl indole under multi-site phase-transfer catalyst: A kinetic study

Journal Title: Journal of Medicinal and Chemical Sciences - Year 2019, Vol 2, Issue 1

Abstract

The ultrasound assisted preparation of 1-benzyl-1-indole (arylation) from the reaction of benzyl chloride (BC) and indole was carried out successfully using solid sodium hydroxide and catalyzed by multi-site phase-transfer catalyst (MPTC) viz., 1,4-benzyl-1,4-diazoniab-icyclo[2.2.2]octanium dichloride in a solid–liquid reaction condition (SL-PTC). Water was introduced in a trace quantity to the reaction system to avoid a serious hydration of active intermediate. The potentiality of the multi–site phase-transfer catalyst was demonstrated by following the kinetics arylation of indole under pseudo–first order conditions by employing aqueous sodium hydroxide and indole in excess. The reaction was monitored by gas Chromatography. The synthesized MPTC and 1-benzyl-1-indole were characterized by 1H NMR and 13C NMR. The reaction is greatly enhanced in the solid–liquid system, catalyzed by multi-site quaternary ammonium salt (MPTC) and ultrasound irradiation (28 kHz, 300W) in a batch reactor.

Authors and Affiliations

Manickam Sathiyaraj, Perumal Venkatesh

Keywords

Related Articles

Anomalous reactivity of benzopinacolone towards 4-phenylthiosemicarbazide, a nucleophile endowed with alpha-effect

In a medicinal chemistry-driven drug discovery program aimed at synthesizing new topically-acting trypanocidal chemotherapeutic agents to treat the African trypanosomiasis, our research group became interested in new che...

An overview on the effects of power frequency electromagnetic field exposure on the female reproduction system, pregnancy outcome and fetal development

This article presents a review of the published scientific studies on the potential adverse effects of power frequency electromagnetic field (50-60 Hz) from domestic and occupational sources and electric transmission lin...

A mini review: recent developments of heterocyclic chemistry in some drug discovery scaffolds synthesis

Novel developments in the synthetic techniques that facilitate rapid access to various functionalized heterocyclic compounds are essential in medicinal chemistry. They enable an expansion of the available drug-associated...

Photosensitization of phthalocyanine for singlet oxygen generation in photodynamic therapy applications

In this work, phthalocyanine and its OCH3 derivatives were investigated to see their photosensitization characteristics for producing singlet molecular oxygen, which is important in photodynamic therapy type-II. All stru...

Synthesis of icosadeuterio-benzopinacol (Benzopinacol-d20)

This work reports on synthesis of high yield (92%) of isosadeuterio-benzopinacol (benzopinacol-d20) via photo-reductive dimerization of benzophenone-d10. The latter compound was obtained using an improved method to achie...

Download PDF file
  • EP ID EP491188
  • DOI 10.26655/JMCHEMSCI.2019.6.5
  • Views 127
  • Downloads 0

How To Cite

Manickam Sathiyaraj, Perumal Venkatesh (2019). Ultrasound assisted synthesis of N-aryl indole under multi-site phase-transfer catalyst: A kinetic study. Journal of Medicinal and Chemical Sciences, 2(1), 27-34. https://europub.co.uk/articles/-A-491188