Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

Abstract

Oxone is a commercially available oxidant, composed of a mixture of three inorganic species, being the potassium peroxymonosulfate (KHSO5) the reactive one. Over the past few decades, this cheap and environmentally friendly oxidant has become a powerful tool in organic synthesis, being extensively employed to mediate the construction of a plethora of important compounds. This review summarizes the recent advances in the Oxone-mediated synthesis of N-, O- and chalcogen-containing heterocyclic compounds, through a wide diversity of reactions, starting from several kinds of substrate, highlighting the main synthetic differences, advantages, the scope and limitations.

One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides

“…The reaction was then tested using 80 % of amplitude in the US probe, and the product 1 a was obtained in 69 % yield after 1 h (Table 1, entry 7). Finally, different solvents were tested in the reaction, including methanol, water, acetonitrile, acetic acid, dimethylformamide, glycerol, polyethylene glycol 400 (PEG-400), and a mixture of ethanol:water (1 : 1) (Table 1, entries [8][9][10][11][12][13][14][15]. Among the tested solvents, methanol was the first in class, affording the expected isoquinoline derivative 1 a in 92 % yield (Table 1, entry 8).…”

“…Therefore, we wonder if the system Oxone®/RYYR (Y=Se, Te)/US could be used in a one‐pot sequential synthesis of organochalcogenyl isoquinolinium imides (Scheme 1d). Here, we describe our outcomes in the transition‐metal‐free, electrophilic cyclization of N ′‐(2‐alkynylbenzylidene)hydrazides with electrophilic selenium and tellurium species generated in situ under ultrasound [15] …”

“…Here, we describe our outcomes in the transition-metal-free, electrophilic cyclization of N'-(2alkynylbenzylidene)hydrazides with electrophilic selenium and tellurium species generated in situ under ultrasound. [15]…”

Radical cyclization of alkynyl aryl ketones for the synthesis of 3-seleno-substituted thiochromones and chromones

“…Therefore, considering the importance of organoselenium compounds and thiochromone/chromone derivatives, and our interest in the synthesis of seleno-functionalized heterocyclic compounds, 19 we describe here an alternative method for the synthesis of 3-organylselanylthiochromones 3 and 3-organylselanylchromones 5 . The protocol involves the cyclization of different alkynyl aryl ketones 1 and 4 with selenium radical species generated in situ through the reaction of diorganyl diselenides 2 with Oxone® as the green oxidizing agent, 20 using acetonitrile as the solvent at 82 °C in an open atmosphere, as shown in Scheme 1C.…”

Green Synthesis of Pyrazoles: Recent Developments in Aqueous Methods

“…The utilization of ecofriendly synthetic techniques like 'green chemistry' has come into consideration for the synthetic chemist to develop products with these desired qualities. [1][2][3][4][5] The green approaches that are generally considered for organic synthetic reactions are: (i) the use of green solvents, such as nature's solvent water, as a reaction medium instead of organic solvents, (ii) reactions in the solid state without the use of solvent, (iii) using catalytic amount of organometallic reagents instead of stoichiometric amounts, and (iv) biosynthetic processes. For the synthesis of heterocyclic compounds, many green methods have been applied, [6][7][8][9] performing the reactions at ambient temperature and using alternative energy sources are the methods of choice.…”