One-Pot MulticomponentSynthesis of Fully Substituted1,3-Thiazoles Appended with Naturally Occurring Lawsone

Lawsone is a popular bioactive natural product. 1,3-Thiazoles are also widely distributed in many natural products, FDA-approved drugs, and functional materials. We report herein the first synthesis of naturally occurring lawsone-linked fully substituted 1,3-thiazoles in a one-pot multicomponent reaction (MCR) of arylglyoxals, lawsone, and thiobenzamides in acetic acid at 90 °C, affording lawsone–1,3-thiazole hybrids in excellent yields in short reaction times. The advantages of the present method include facile, robust, and easy access to the medicinally relevant diverse array of fully substituted lawsone–1,3-thiazole hybrids, easy isolation of the product by filtration, thereby avoiding column-chromatographic purifications, short reaction time, and metal- and catalyst-free and gram-scale synthesis.

Publication Details

Journal
Figshare
Published
2025-02-07
DOI
https://doi.org/10.1021/acs.joc.4c02927.s001
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
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article

One-Pot MulticomponentSynthesis of Fully Substituted1,3-Thiazoles Appended with Naturally Occurring Lawsone

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Multicomponent Synthesis of Heterocycles
article

One-Pot MulticomponentSynthesis of Fully Substituted1,3-Thiazoles Appended with Naturally Occurring Lawsone

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Abstract

Lawsone is a popular bioactive natural product. 1,3-Thiazoles are also widely distributed in many natural products, FDA-approved drugs, and functional materials. We report herein the first synthesis of naturally occurring lawsone-linked fully substituted 1,3-thiazoles in a one-pot multicomponent reaction (MCR) of arylglyoxals, lawsone, and thiobenzamides in acetic acid at 90 °C, affording lawsone–1,3-thiazole hybrids in excellent yields in short reaction times. The advantages of the present method include facile, robust, and easy access to the medicinally relevant diverse array of fully substituted lawsone–1,3-thiazole hybrids, easy isolation of the product by filtration, thereby avoiding column-chromatographic purifications, short reaction time, and metal- and catalyst-free and gram-scale synthesis.

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Openalex Percentile: Top 58%
Multicomponent Synthesis of Heterocycles
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