Efficient construction of highly functionalized pyrrolo[1,2- c ]imidazol-1-ones via a regioselective 1,3-dipolar cycloaddition of imidazolidin-4-ones, aldehydes, and nitroalkenes in one pot
| Autor: | Ying Liu, Jie Liu, Yanyang He, Xia Zhang, Xiaoyan Wang, Jianyou Shi |
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| Rok vydání: | 2016 |
| Předmět: |
1h nmr spectroscopy
010405 organic chemistry Chemistry Organic Chemistry Regioselectivity 010402 general chemistry Nitroalkene 01 natural sciences Biochemistry Medicinal chemistry Cycloaddition 0104 chemical sciences Stereocenter chemistry.chemical_compound Yield (chemistry) Drug Discovery 1 3-Dipolar cycloaddition Organic chemistry |
| Zdroj: | Tetrahedron Letters. 57:1143-1145 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2016.01.103 |
| Popis: | A series of novel pyrrolo[1,2-c]imidazol-1-ones were efficiently synthesized via a three-component, regioselective 1,3-dipolar cycloaddition reaction. The azomethine ylides generated in situ from imidazolidin-4-ones and aldehydes reacted with the nitroalkenes to yield the novel pyrrolo[1,2-c]imidazol-1-one derivatives with multiple stereogenic centers in moderate to high yields (up to 99%) and in high diastereoselectivities (up to 98:2). The structure and relative stereochemistry of cycloadducts were confirmed by 1H NMR spectroscopy and X-ray crystallography. |
| Databáze: | OpenAIRE |
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