Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives
Bromination of N-substituted homophthalimides and tetrahydropyrido[4,3-d]- pyrimidine-5,7-diones produces 4,4-dibromohomophthalimide and 8,8-dibromo-tetrahydropyrido[4,3-d]pyrimidine-5,7-dione derivatives, respectively, that can be used as precursors for spiro derivatives. The dibromo derivatives re...
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MDPI AG
2015-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/2/1842 |
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| author | Rasha M. Faty Mohamed S. Rashed Mohamed M. Youssef |
| author_facet | Rasha M. Faty Mohamed S. Rashed Mohamed M. Youssef |
| author_sort | Rasha M. Faty |
| collection | DOAJ |
| description | Bromination of N-substituted homophthalimides and tetrahydropyrido[4,3-d]- pyrimidine-5,7-diones produces 4,4-dibromohomophthalimide and 8,8-dibromo-tetrahydropyrido[4,3-d]pyrimidine-5,7-dione derivatives, respectively, that can be used as precursors for spiro derivatives. The dibromo derivatives react with different binucleophilic reagents to produce several spiroisoquinoline and spirotetrahydropyrido[4,3-d]- pyrimidine-5,7-dione derivatives, respectively. Reaction of the dibromo derivatives with malononitrile produces dicyanomethylene derivatives which react with different binucleophiles to produce new spiro derivatives. All new compounds are prepared by using the usual chemical conditions and microwave assisted conditions. The latter conditions improved the reaction yields, reduced reaction times and ameliorated the effects on the surrounding environment as the reactions are carried out in closed systems. Structures of the newly synthesized compounds are proved using spectroscopic methods such as IR, MS, 1H-NMR and 13C-NMR and elemental analyses. Some of the newly synthesized compounds were tested for their antimicrobial activities, whereby four of them showed moderate activities and the rest showed low or no activities towards the investigated species. |
| first_indexed | 2024-12-16T14:23:06Z |
| format | Article |
| id | doaj.art-1801ab946bf84427bde57b137ad469f1 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-16T14:23:06Z |
| publishDate | 2015-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1801ab946bf84427bde57b137ad469f12022-12-21T22:28:26ZengMDPI AGMolecules1420-30492015-01-012021842185910.3390/molecules20021842molecules20021842Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine DerivativesRasha M. Faty0Mohamed S. Rashed1Mohamed M. Youssef2Chemistry Department, Faculty of Science, Cairo University, Cairo 12613, EgyptSchlumberger, Well Services, Al-Khobar 31952, Saudi ArabiaChemistry Department, Faculty of Science, Cairo University, Cairo 12613, EgyptBromination of N-substituted homophthalimides and tetrahydropyrido[4,3-d]- pyrimidine-5,7-diones produces 4,4-dibromohomophthalimide and 8,8-dibromo-tetrahydropyrido[4,3-d]pyrimidine-5,7-dione derivatives, respectively, that can be used as precursors for spiro derivatives. The dibromo derivatives react with different binucleophilic reagents to produce several spiroisoquinoline and spirotetrahydropyrido[4,3-d]- pyrimidine-5,7-dione derivatives, respectively. Reaction of the dibromo derivatives with malononitrile produces dicyanomethylene derivatives which react with different binucleophiles to produce new spiro derivatives. All new compounds are prepared by using the usual chemical conditions and microwave assisted conditions. The latter conditions improved the reaction yields, reduced reaction times and ameliorated the effects on the surrounding environment as the reactions are carried out in closed systems. Structures of the newly synthesized compounds are proved using spectroscopic methods such as IR, MS, 1H-NMR and 13C-NMR and elemental analyses. Some of the newly synthesized compounds were tested for their antimicrobial activities, whereby four of them showed moderate activities and the rest showed low or no activities towards the investigated species.http://www.mdpi.com/1420-3049/20/2/1842brominationhomophthalimidepyrido[4,3-d]pyrimidinespiro compoundsmicrowaveantimicrobial |
| spellingShingle | Rasha M. Faty Mohamed S. Rashed Mohamed M. Youssef Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives Molecules bromination homophthalimide pyrido[4,3-d]pyrimidine spiro compounds microwave antimicrobial |
| title | Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives |
| title_full | Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives |
| title_fullStr | Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives |
| title_full_unstemmed | Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives |
| title_short | Microwave-Assisted Synthesis and Antimicrobial Evaluation of Novel Spiroisoquinoline and Spiropyrido[4,3-d]pyrimidine Derivatives |
| title_sort | microwave assisted synthesis and antimicrobial evaluation of novel spiroisoquinoline and spiropyrido 4 3 d pyrimidine derivatives |
| topic | bromination homophthalimide pyrido[4,3-d]pyrimidine spiro compounds microwave antimicrobial |
| url | http://www.mdpi.com/1420-3049/20/2/1842 |
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