PTSA-Catalyzed Cyclization of 6-Aminouracils with Diimines: Efficient Synthesis of Functionalized Tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones
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| Natura: | Recurso digital |
| Lingua: | inglese |
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2018
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| _version_ | 1866901130797121536 |
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| author | Khodabakhshi, Mohammad R. Kiamehr, Mostafa Moghaddam, Firouz M. Villinger, Alexander Langer, Peter |
| author_facet | Khodabakhshi, Mohammad R. Kiamehr, Mostafa Moghaddam, Firouz M. Villinger, Alexander Langer, Peter |
| contents | A new and efficient method has been developed for the synthesis of 5,7-diaryl-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4-dione derivatives by cyclization of 6-aminouracils with N,N?-bis(arylmethylidene)arylmethanes (diimines). The products were formed in good yields and with very good anti-diastereoselectivity. The best yields were obtained when p-toluenesulfonic acid (PTSA) was used as the catalyst. The solvent also played an important role in the optimization. An amino-substituted 6-aminouracil and a corresponding sulfur analog could be successfully employed. In addition, various diimines, electron rich and neutral, could be successfully employed. The products are of relevance as analogs of biologically active drugs and natural products. 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
| format | Recurso digital |
| id | zenodo_https___doi_org_10_1002_slct_201801869 |
| institution | Zenodo |
| language | eng |
| publishDate | 2018 |
| publisher | Zenodo |
| record_format | zenodo |
| spellingShingle | PTSA-Catalyzed Cyclization of 6-Aminouracils with Diimines: Efficient Synthesis of Functionalized Tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones Khodabakhshi, Mohammad R. Kiamehr, Mostafa Moghaddam, Firouz M. Villinger, Alexander Langer, Peter aminouracil cyclization heterocycles nucleobases pyrimidines A new and efficient method has been developed for the synthesis of 5,7-diaryl-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4-dione derivatives by cyclization of 6-aminouracils with N,N?-bis(arylmethylidene)arylmethanes (diimines). The products were formed in good yields and with very good anti-diastereoselectivity. The best yields were obtained when p-toluenesulfonic acid (PTSA) was used as the catalyst. The solvent also played an important role in the optimization. An amino-substituted 6-aminouracil and a corresponding sulfur analog could be successfully employed. In addition, various diimines, electron rich and neutral, could be successfully employed. The products are of relevance as analogs of biologically active drugs and natural products. 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
| title | PTSA-Catalyzed Cyclization of 6-Aminouracils with Diimines: Efficient Synthesis of Functionalized Tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones |
| topic | aminouracil cyclization heterocycles nucleobases pyrimidines |
| url | https://doi.org/10.1002/slct.201801869 |