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

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

Organic chemistry

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.

DOI

10.21608/ejchem.2020.26980.2555

Keywords

α-Oxoketene gem-dithiols, dihydrpyrimidine, 1, 2-dithiol-3-thione, Indole, 3-indole aldehyde and Kneovenagel's condensation

Authors

First Name

Entesar

Last Name

Hassan

MiddleName

-

Affiliation

Chemistry Department, Faculty of Science, South Valley University, Qena

Email

entesar.abdelshafy@gmail.com

City

-

Orcid

-

First Name

Salem

Last Name

Zayed

MiddleName

-

Affiliation

Chemistry Department, Faculty of Science, South Valley University, Qena

Email

sezayed@yahoo.com

City

-

Orcid

-

First Name

Asmaa

Last Name

Abozied

MiddleName

-

Affiliation

Chemistry Department, Faculty of Science, South Valley University, Qena.

Email

a_abozied@yahoo.com

City

-

Orcid

-

Volume

63

Article Issue

11

Related Issue

18119

Issue Date

2020-11-01

Receive Date

2020-03-31

Publish Date

2020-11-01

Page Start

4,509

Page End

4,520

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_86649.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=86649

Order

31

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

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

Details

Type

Article

Created At

22 Jan 2023