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Synthesis of Substituted Azetidinones Derived from Dimer of Apremilast |
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1 | Title | Title of Document | Synthesis of Substituted Azetidinones Derived from Dimer of Apremilast |
2 | Creator | Author's name, affiliation, country | YELLANKI JAGANNADHAM1,2, DODDA VIVEKANANDA REDDY2, BHOOMIREDDY RAMADEVI2 and BETHANAMUDI PRASANNA*1,2 1Research Center, Department of Chemistry, Chaitanya Post Graduate College (Autonomous), Kishanpura, Hanamkonda, Warangal Telangana State-506 001, India
2Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad, Telanagan State-500085, India
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3 | Subject | Dicipline(s) | Chemical Science |
3 | Subject | Keywords | Biisoindoline, Azetidinones, Aminophthalic acid, Schiff base, Chloroacetyl chloride, Dehydrative annulation |
4 | Description | Abstract | Over the past decade, design of 2-azetidinones scaffold has attracted greater interest of synthesis because of more biological and pharmacological potencies. Specifically, sulfonamide rings and their derivatives represent a medicinally and pharmaceutically important class of heterocyclic motifs that are found as the core structural skeletons in a variety of several naturally occurring alkaloids. We effectively intended 4-(3-chloro-2-oxo-4-aryllazetidin-1-yl)-2/-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethyl)-2,4`-biisoindoline-1.1`3,3-tetraones (6(a-f)). 4-Amino-2`-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2,4`-biisoindo line-1, 1`, 3, 3`-tetraone 3 was prepared by condensation of 3-aminophthalic acid 2 with 1,3-ethoxy-4-methoxyphenyl)-2-methylsutfonylethylamine 1 by a single step. Condensation of compound 3 with various aromatic aldehydes gives substituted Schiff base of 2`-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2,4-biisoindoline-1,1`,3,3`-tetraones (5(a-f)) which upon dehydrative annulation in the presence of chloroacetylchloride in the presence of triethylamine in DCM solvent yielded 4-(3-Chloro-2-oxo-4-aryllazetidin-1-yl)-2`-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethyl)-2,4`-biisoindoline-1.1`3,3`-tetraones 6(a-f). All the synthesized compounds were recognized by Infra Red-Vibrational spectroscopy, Proton Nuclear Magnetic Resonance, mass spectroscopy and their C, H, N analyses |
5 | Publishers | Organizing agency, location | WWW Publications, India |
6 | Contributor | Sponsor(s) | - |
7 | Date | Date (YYYY-MM-DD) | - |
8 | Type | Status & genre | Peer-reviewed Article |
8 | Type | Type | |
9 | Formate | File Formate | PDF |
10 | Identifier | Uniform Resource Identifier | Click Here |
10 | Identifier | Digital Object Identifier | |
11 | Source | Journal/conference title; vol., no. (Year) | Chemical Science Transactions, Volume 8 , Number (3), (2019) |
12 | Lanuguage | English=en | en |
13 | Relation | Supp.files | |
14 | Coverage | | - |
15 | Copyright | Copyright and permissions | |
Chemical Science Transactions | Chem Sci Trans | CST | Online Chemistry Journal | Open Access
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