Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations
Hassan, E., Zayed, S., Abozied, A. (2020). Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations. EKB Journal Management System, 63(11), 4509-4520. doi: 10.21608/ejchem.2020.26980.2555
Entesar Hassan; Salem Zayed; Asmaa Abozied. "Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations". EKB Journal Management System, 63, 11, 2020, 4509-4520. doi: 10.21608/ejchem.2020.26980.2555
Hassan, E., Zayed, S., Abozied, A. (2020). 'Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations', EKB Journal Management System, 63(11), pp. 4509-4520. doi: 10.21608/ejchem.2020.26980.2555
Hassan, E., Zayed, S., Abozied, A. Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations. EKB Journal Management System, 2020; 63(11): 4509-4520. doi: 10.21608/ejchem.2020.26980.2555

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

Egyptian Journal of Chemistry
Article 31, Volume 63, Issue 11, November 2020, Page 4509-4520  XML PDF (1.72 MB)
Document Type: Original Article
DOI: 10.21608/ejchem.2020.26980.2555
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Authors
Entesar Hassan email 1; Salem Zayed1; Asmaa Abozied2
1Chemistry Department, Faculty of Science, South Valley University, Qena
2Chemistry Department, Faculty of Science, South Valley University, Qena.
Abstract
In the present work the authors could synthesize the substrates oxoketen gem-dithols 5, ketenedithioacetal 6 and 1,2-dithiol-3-thione 39 from compounds bearing both nucleus indole and dihydropyrimidines together due to their biological and pharmacological activities. In this paper, and as a result of biological and pharmacological activities of oxoketen gem-dithols, ketenedithioacetal and/or 1,2-dithiol-3-thione; we synthesized various derivatives of them via indole and dihydropyrimidine in the form of either condensed or fused derivatives. We used ecofriendly methods such as pure orange juice as a green solvent and as an acid catalyst in the same time to prepare, 1-[2-imino-4-(1H-indol-3-yl)-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl]-ethan-1-one 4a and/or 1-[4-(1H-Indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]-ethan-1-one 4b. Subsequently, the substrate 4b was treated with different reagents to afford, 1-(4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-dimercaptoprop-2-en-1-one 5 and/or 1-(4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-bis(methylthio)prop-2-en-1-one 6. Compounds 5 and/or 6 were used as synthons to get various heterocyclic compounds such as 3-(4-(1H-indol-3-yl)-6-methyl-2-(piperidin-1-yl)-1,4-dihydropyrimidine-5-carbonyl)-2-thioxochroman-4-one 16 and/or 4'-(1H-indol-3-yl)-2-mercapto-6'-methyl-6-(methylthio)-2'-thioxo-1',2',3',4'-tetr-ahydro-[4,5'-bipyrimidin-e]-5-carbaldehyde 18. The newly synthesized compounds have been in vitro examined as antimicrobial agents, and some of them showed a promising activity. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1H-NMR and MS.
Keywords
α-Oxoketene gem-dithiols; dihydrpyrimidine; 1; 2-dithiol-3-thione; indole; 3-indole aldehyde and Kneovenagel's condensation
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