Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines

In this article, we applied ultrasonic irradiation as an ecofriendly, green, efficient approach for the synthesis of a new 1,3-thiazoles and 1,3,4-thiadiazines under solvent-free conditions. Thus, thiocarbohydrazide condenses with N-(thiazol-2-yl)acetamide (2) in different molar ratios under ultraso...

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Autores principales:	Sara N. Shabaan, Basma Saad Baaiu, Anhar Abdel-Aziem, Mohamed S. Abdel-Aziz
Formato:	article
Lenguaje:	EN
Publicado:	Taylor & Francis Group 2021
Materias:	ultrasound irradiation thiazoles hydrazonoyl halides thiadiazines antimicrobial activity Science Q Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/dbc259327eda4ceb9c021f8073a5496d
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spelling	oai:doaj.org-article:dbc259327eda4ceb9c021f8073a5496d2021-12-01T14:40:59ZUltrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines1751-82531751-719210.1080/17518253.2021.1999508https://doaj.org/article/dbc259327eda4ceb9c021f8073a5496d2021-10-01T00:00:00Zhttp://dx.doi.org/10.1080/17518253.2021.1999508https://doaj.org/toc/1751-8253https://doaj.org/toc/1751-7192In this article, we applied ultrasonic irradiation as an ecofriendly, green, efficient approach for the synthesis of a new 1,3-thiazoles and 1,3,4-thiadiazines under solvent-free conditions. Thus, thiocarbohydrazide condenses with N-(thiazol-2-yl)acetamide (2) in different molar ratios under ultrasonic irradiation afforded mono and bis thiocarbohydrazons 3a,b, respectively. Thiocarbohydrazones were reacted with α-haloketone, α-haloester as well as hydrazonoyl halides under ultrasonic conditions afforded 1,3-thiazole 4, 1,3-thiazolinone 5 and 1,3,4-thiadiazines 6 and 11a–c, respectively. The reaction of monohydrazone 3a with phthalic anhydride derivatives afforded phthalazines 7a,b in a good yield. Ultrasonic irradiation has benefits such as greater purity, lower cost, high yields, and simple workups compared to the conventional methods. All the new compounds were screened for antimicrobial activity against different tested microbes. Most of the newly synthesized compounds exhibited potent to moderate activities toward the tested microbes. Compounds that exhibited potent antimicrobial activities were selected to measure their MIC and MBC values. The results revealed that compounds 3a, 3b, 8, 10, and 11a showed lower MIC against Staphylococcus aureus with the values of 39.06, 78.13, 9.77, 39.06 and 39.06 µg/ml, respectively. Meanwhile, the MBC values were found to be acceptable for 3a and 10 of 156 and 312, respectively.Sara N. ShabaanBasma Saad BaaiuAnhar Abdel-AziemMohamed S. Abdel-AzizTaylor & Francis Grouparticleultrasound irradiationthiazoleshydrazonoyl halidesthiadiazinesantimicrobial activityScienceQChemistryQD1-999ENGreen Chemistry Letters and Reviews, Vol 14, Iss 4, Pp 689-698 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	ultrasound irradiation thiazoles hydrazonoyl halides thiadiazines antimicrobial activity Science Q Chemistry QD1-999
spellingShingle	ultrasound irradiation thiazoles hydrazonoyl halides thiadiazines antimicrobial activity Science Q Chemistry QD1-999 Sara N. Shabaan Basma Saad Baaiu Anhar Abdel-Aziem Mohamed S. Abdel-Aziz Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
description	In this article, we applied ultrasonic irradiation as an ecofriendly, green, efficient approach for the synthesis of a new 1,3-thiazoles and 1,3,4-thiadiazines under solvent-free conditions. Thus, thiocarbohydrazide condenses with N-(thiazol-2-yl)acetamide (2) in different molar ratios under ultrasonic irradiation afforded mono and bis thiocarbohydrazons 3a,b, respectively. Thiocarbohydrazones were reacted with α-haloketone, α-haloester as well as hydrazonoyl halides under ultrasonic conditions afforded 1,3-thiazole 4, 1,3-thiazolinone 5 and 1,3,4-thiadiazines 6 and 11a–c, respectively. The reaction of monohydrazone 3a with phthalic anhydride derivatives afforded phthalazines 7a,b in a good yield. Ultrasonic irradiation has benefits such as greater purity, lower cost, high yields, and simple workups compared to the conventional methods. All the new compounds were screened for antimicrobial activity against different tested microbes. Most of the newly synthesized compounds exhibited potent to moderate activities toward the tested microbes. Compounds that exhibited potent antimicrobial activities were selected to measure their MIC and MBC values. The results revealed that compounds 3a, 3b, 8, 10, and 11a showed lower MIC against Staphylococcus aureus with the values of 39.06, 78.13, 9.77, 39.06 and 39.06 µg/ml, respectively. Meanwhile, the MBC values were found to be acceptable for 3a and 10 of 156 and 312, respectively.
format	article
author	Sara N. Shabaan Basma Saad Baaiu Anhar Abdel-Aziem Mohamed S. Abdel-Aziz
author_facet	Sara N. Shabaan Basma Saad Baaiu Anhar Abdel-Aziem Mohamed S. Abdel-Aziz
author_sort	Sara N. Shabaan
title	Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
title_short	Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
title_full	Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
title_fullStr	Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
title_full_unstemmed	Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
title_sort	ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines
publisher	Taylor & Francis Group
publishDate	2021
url	https://doaj.org/article/dbc259327eda4ceb9c021f8073a5496d
work_keys_str_mv	AT saranshabaan ultrasoundassistedgreensynthesisandantimicrobialassessmentof13thiazolesand134thiadiazines AT basmasaadbaaiu ultrasoundassistedgreensynthesisandantimicrobialassessmentof13thiazolesand134thiadiazines AT anharabdelaziem ultrasoundassistedgreensynthesisandantimicrobialassessmentof13thiazolesand134thiadiazines AT mohamedsabdelaziz ultrasoundassistedgreensynthesisandantimicrobialassessmentof13thiazolesand134thiadiazines
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Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines

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