Synthesis and crystal structure of (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-b]pyran-2-carboxamide
| Autor: | Jack H. Roireau, Scott Kassel, Robert M. Giuliano, Michael W. Giuliano, Mark W. Bezpalko, John Greene, Noa Kopplin |
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| Rok vydání: | 2020 |
| Předmět: |
crystal structure
Nitrile medicine.drug_class Carboxamide Crystal structure 010402 general chemistry pyranopyran 01 natural sciences diplopyrone Research Communications chemistry.chemical_compound Amide medicine General Materials Science Crystallography Bicyclic molecule 010405 organic chemistry Hydrogen bond General Chemistry Condensed Matter Physics 0104 chemical sciences chemistry pyranopyran QD901-999 Pyran Acetaldoxime |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 76, Iss 5, Pp 761-764 (2020) Acta Crystallographica Section E: Crystallographic Communications |
| ISSN: | 2056-9890 |
| Popis: | (2S,4aR,8aR)-6-Oxo-2,4a,6,8a-tetrahydropyrano[3,2-b]pyran-2-carboxamide, a potentially effective antibacterial agent, was prepared by a chemoselective hydration of the corresponding nitrile using a heterogeneous catalytic method based on copper(II) supported on molecular sieves, in the presence of acetaldoxime. It belongs to a new class of pyranopyrans that possess antibacterial and phytotoxic activity. The pyranopyran amide (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-b]pyran-2-carboxamide, C9H9NO4, 3, was prepared by a chemoselective hydration of the corresponding nitrile, 2, using a heterogeneous catalytic method based on copper(II) supported on molecular sieves, in the presence of acetaldoxime. Compound 3 belongs to a new class of pyranopyrans that possess antibacterial and phytotoxic activity. Crystallographic analysis of 3 shows a bent structure for the cis-fused bicyclic pyranopyran, similar to nitrile 2. Evidence of an intramolecular hydrogen bond involving the amide group and ring oxygen was not observed; however, two separate intermolecular hydrogen-bonding interactions were observed between the amide hydrogen atoms and adjacent carbonyl oxygen atoms along the b- and a-axis directions. The latter interaction may also be supported by an intermolecular C—H⋯O hydrogen bond. The lattice is filled out by close-packed layers of this hydrogen-bonded network along the c-axis direction, related from one to the next by a 21 screw axis. |
| Databáze: | OpenAIRE |
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