What question did this study set out to answer?

To develop a direct, safe synthetic protocol for preparing 3-organylselanylthiochromones and 3-organylselanylchromones through radical cyclization.

January 1, 2022Organic & Biomolecular Chemistry

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

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To develop a direct, safe synthetic protocol for preparing 3-organylselanylthiochromones and 3-organylselanylchromones through radical cyclization.
Promoted radical cyclization of alkynyl aryl ketones containing an ortho-thiopropyl or methoxy group with diorganyl diselenides.
Conducted reactions using Oxone as a non-hazardous oxidant in acetonitrile (CH3CN) at 82 °C.
Evaluated substrate scope, scale-up capability at 3.0 mmol, and post-synthetic oxidation utility.
Synthesized twenty-one new 3-organylselanylthiochromones and selanylchromones with chemical yields ranging from 55% to 95%.
Demonstrated reaction scalability to 3.0 mmol, producing the desired product in 80% yield.
Confirmed synthetic utility through subsequent oxidation of 2-phenyl-3-(phenylselanyl)-4H-thiochromen-4-one.

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Implication

Experimental study demonstrates the synthesis of 3-seleno-substituted thiochromones and chromones via radical cyclization, highlighting a scalable and safe oxidative route.

Cite This Study

Bartz et al. (2022) studied this question.

synapsesocial.com/papers/69deebd2488ed2d92be9443f https://doi.org/10.1039/d2ob01762h

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Implication

Experimental study demonstrates the synthesis of 3-seleno-substituted thiochromones and chromones via radical cyclization, highlighting a scalable and safe oxidative route.

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

Key Points

Discussion

Implication

Cite This Study

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

Key Points

Discussion

Implication

Cite This Study

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