One-Pot Multicomponent Synthesis of Fully Substituted 1,3-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.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-06
DOI
https://doi.org/10.1021/acs.joc.4c02927
Citations
17
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
15.91

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article

One-Pot Multicomponent Synthesis of Fully Substituted 1,3-Thiazoles Appended with Naturally Occurring Lawsone

Bibhuti Bhusan Parida, Swadhin Swaraj Acharya, Bisal Kumar Guin
17 citations
The Journal of Organic Chemistry
Multicomponent Synthesis of Heterocycles
15.91
article

One-Pot Multicomponent Synthesis of Fully Substituted 1,3-Thiazoles Appended with Naturally Occurring Lawsone

Bibhuti Bhusan Parida, Swadhin Swaraj Acharya, Bisal Kumar Guin
article en
17 citations

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.

The Journal of Organic ChemistryVol. 90(7)
Berhampur University (IN)
Council of Scientific and Industrial Research, India, University Grants Commission, Science and Engineering Research Board
Openalex Percentile: Top 1%
Multicomponent Synthesis of Heterocycles
15.91
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