Recoverable Fe(III)–porphyrin complex using a rapid, highly yielded, and green synthesis of dihydrotetrazolo[1,5-a]thiazolo[4,5-d]pyrimidine-6(4H)-thione derivatives.
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| Title: | Recoverable Fe(III)–porphyrin complex using a rapid, highly yielded, and green synthesis of dihydrotetrazolo[1,5-a]thiazolo[4,5-d]pyrimidine-6(4H)-thione derivatives. |
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| Authors: | Adam, Mohamed Shaker S.1 (AUTHOR) madam@kfu.edu.sa, Khalil, Ahmed1 (AUTHOR) akkhalil@kfu.edu.sa, Nassar, Mostafa Y.1 (AUTHOR) mynassar@kfu.edu.sa, Alkhalifah, Mohammed A.1 (AUTHOR) malkalifah@kfu.edu.sa, Eskander, Thomas Nady A.2 (AUTHOR) thomas.nady20@gmail.com, El-Remaily, Mahmoud Abd El Aleem Ali Ali2,3 (AUTHOR) mahmoud_ali@science.sohag.edu.eg |
| Source: | Research on Chemical Intermediates. May2026, Vol. 52 Issue 5, p3501-3525. 25p. |
| Subjects: | Iron porphyrins, Heterocyclic compounds, Sustainable chemistry, Sustainability, Chemical synthesis, Catalytic activity, Catalysts recycling |
| Abstract: | An environmentally benign and highly efficient synthetic protocol has been established for the preparation of new dihydrotetrazolo[1,5-a]thiazolo[4,5-d]pyrimidine-6(4H)-thione derivatives via a one-pot, three-component condensation of rhodanine, 5-aminotetrazole, and various aromatic aldehydes catalyzed by a recoverable Fe(III)–porphyrin complex. Comprehensive characterization of the catalytic products was performed using FT-IR, 1H-NMR, 13C-NMR, and micro-elemental analyses, confirming their proposed structures. The optimized catalytic system, operating in an ethanol–water (3:1, v/v) medium at 80 °C, afforded the desired products in excellent yields (91–97%) within short reaction times (10–25 min). Systematic optimization studies revealed that increasing the catalyst loading from 3 mmol to 10 mmol% significantly improved the product yield (from 14 to 97%) and reduced the reaction time, identifying 10 mmol% as the optimal catalyst dosage. Comparative screening demonstrated that the Fe(III)–porphyrin catalyst markedly outperformed other Lewis acids, bases, and ionic liquid catalysts, including FeCl3·6H2O, Fe(OTf)3, Mg(OTf)2, and ZnBr2, which achieved superior conversion efficiency and selectivity under mild conditions. Hot filtration experiments confirmed that the catalytic process proceeds predominantly via a homogeneous mechanism, as the reaction continued to progress even after the catalyst was removed. The Fe(III)–porphyrin catalyst exhibited excellent stability and could be reused for at least five consecutive cycles without significant loss of activity. This green and high-yielding methodology not only minimizes solvent waste but also highlights the potential of Fe(III)–porphyrin complexes as robust, recyclable, and eco-friendly catalysts for the sustainable synthesis of pharmacologically significant heterocycles. [ABSTRACT FROM AUTHOR] |
| Copyright of Research on Chemical Intermediates is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
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| Header | DbId: egs DbLabel: Engineering Source An: 193085582 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Recoverable Fe(III)–porphyrin complex using a rapid, highly yielded, and green synthesis of dihydrotetrazolo[1,5-a]thiazolo[4,5-d]pyrimidine-6(4H)-thione derivatives. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Adam%2C+Mohamed+Shaker+S%2E%22">Adam, Mohamed Shaker S.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> madam@kfu.edu.sa</i><br /><searchLink fieldCode="AR" term="%22Khalil%2C+Ahmed%22">Khalil, Ahmed</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> akkhalil@kfu.edu.sa</i><br /><searchLink fieldCode="AR" term="%22Nassar%2C+Mostafa+Y%2E%22">Nassar, Mostafa Y.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> mynassar@kfu.edu.sa</i><br /><searchLink fieldCode="AR" term="%22Alkhalifah%2C+Mohammed+A%2E%22">Alkhalifah, Mohammed A.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> malkalifah@kfu.edu.sa</i><br /><searchLink fieldCode="AR" term="%22Eskander%2C+Thomas+Nady+A%2E%22">Eskander, Thomas Nady A.</searchLink><relatesTo>2</relatesTo> (AUTHOR)<i> thomas.nady20@gmail.com</i><br /><searchLink fieldCode="AR" term="%22El-Remaily%2C+Mahmoud+Abd+El+Aleem+Ali+Ali%22">El-Remaily, Mahmoud Abd El Aleem Ali Ali</searchLink><relatesTo>2,3</relatesTo> (AUTHOR)<i> mahmoud_ali@science.sohag.edu.eg</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Research+on+Chemical+Intermediates%22">Research on Chemical Intermediates</searchLink>. May2026, Vol. 52 Issue 5, p3501-3525. 25p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Iron+porphyrins%22">Iron porphyrins</searchLink><br /><searchLink fieldCode="DE" term="%22Heterocyclic+compounds%22">Heterocyclic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Sustainable+chemistry%22">Sustainable chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Sustainability%22">Sustainability</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+synthesis%22">Chemical synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Catalytic+activity%22">Catalytic activity</searchLink><br /><searchLink fieldCode="DE" term="%22Catalysts+recycling%22">Catalysts recycling</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: An environmentally benign and highly efficient synthetic protocol has been established for the preparation of new dihydrotetrazolo[1,5-a]thiazolo[4,5-d]pyrimidine-6(4H)-thione derivatives via a one-pot, three-component condensation of rhodanine, 5-aminotetrazole, and various aromatic aldehydes catalyzed by a recoverable Fe(III)–porphyrin complex. Comprehensive characterization of the catalytic products was performed using FT-IR, 1H-NMR, 13C-NMR, and micro-elemental analyses, confirming their proposed structures. The optimized catalytic system, operating in an ethanol–water (3:1, v/v) medium at 80 °C, afforded the desired products in excellent yields (91–97%) within short reaction times (10–25 min). Systematic optimization studies revealed that increasing the catalyst loading from 3 mmol to 10 mmol% significantly improved the product yield (from 14 to 97%) and reduced the reaction time, identifying 10 mmol% as the optimal catalyst dosage. Comparative screening demonstrated that the Fe(III)–porphyrin catalyst markedly outperformed other Lewis acids, bases, and ionic liquid catalysts, including FeCl3·6H2O, Fe(OTf)3, Mg(OTf)2, and ZnBr2, which achieved superior conversion efficiency and selectivity under mild conditions. Hot filtration experiments confirmed that the catalytic process proceeds predominantly via a homogeneous mechanism, as the reaction continued to progress even after the catalyst was removed. The Fe(III)–porphyrin catalyst exhibited excellent stability and could be reused for at least five consecutive cycles without significant loss of activity. This green and high-yielding methodology not only minimizes solvent waste but also highlights the potential of Fe(III)–porphyrin complexes as robust, recyclable, and eco-friendly catalysts for the sustainable synthesis of pharmacologically significant heterocycles. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Research on Chemical Intermediates is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1007/s11164-025-05831-x Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 25 StartPage: 3501 Subjects: – SubjectFull: Iron porphyrins Type: general – SubjectFull: Heterocyclic compounds Type: general – SubjectFull: Sustainable chemistry Type: general – SubjectFull: Sustainability Type: general – SubjectFull: Chemical synthesis Type: general – SubjectFull: Catalytic activity Type: general – SubjectFull: Catalysts recycling Type: general Titles: – TitleFull: Recoverable Fe(III)–porphyrin complex using a rapid, highly yielded, and green synthesis of dihydrotetrazolo[1,5-a]thiazolo[4,5-d]pyrimidine-6(4H)-thione derivatives. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Adam, Mohamed Shaker S. – PersonEntity: Name: NameFull: Khalil, Ahmed – PersonEntity: Name: NameFull: Nassar, Mostafa Y. – PersonEntity: Name: NameFull: Alkhalifah, Mohammed A. – PersonEntity: Name: NameFull: Eskander, Thomas Nady A. – PersonEntity: Name: NameFull: El-Remaily, Mahmoud Abd El Aleem Ali Ali IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 05 Text: May2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 09226168 Numbering: – Type: volume Value: 52 – Type: issue Value: 5 Titles: – TitleFull: Research on Chemical Intermediates Type: main |
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