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Synthesis and crystal structure of (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetra-hydro-pyrano[3,2-b]pyran-2-carboxamide.


ABSTRACT: The pyran-opyran amide (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetra-hydro-pyrano[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 mol-ecular sieves, in the presence of acetaldoxime. Compound 3 belongs to a new class of pyran-opyrans that possess anti-bacterial and phytotoxic activity. Crystallographic analysis of 3 shows a bent structure for the cis-fused bicyclic pyran-opyran, similar to nitrile 2. Evidence of an intra-molecular hydrogen bond involving the amide group and ring oxygen was not observed; however, two separate inter-molecular hydrogen-bonding inter-actions were observed between the amide hydrogen atoms and adjacent carbonyl oxygen atoms along the b- and a-axis directions. The latter inter-action may also be supported by an inter-molecular 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.

SUBMITTER: Greene J 

PROVIDER: S-EPMC7199262 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Synthesis and crystal structure of (2<i>S</i>,4a<i>R</i>,8a<i>R</i>)-6-oxo-2,4a,6,8a-tetra-hydro-pyrano[3,2-<i>b</i>]pyran-2-carboxamide.

Greene John J   Kopplin Noa N   Roireau Jack J   Bezpalko Mark M   Kassel Scott S   Giuliano Michael W MW   Giuliano Robert R  

Acta crystallographica. Section E, Crystallographic communications 20200430 Pt 5


The pyran-opyran amide (2<i>S</i>,4a<i>R</i>,8a<i>R</i>)-6-oxo-2,4a,6,8a-tetra-hydro-pyrano[3,2-<i>b</i>]pyran-2-carboxamide, C<sub>9</sub>H<sub>9</sub>NO<sub>4</sub>, <b>3</b>, was prepared by a chemoselective hydration of the corresponding nitrile, <b>2</b>, using a heterogeneous catalytic method based on copper(II) supported on mol-ecular sieves, in the presence of acetaldoxime. Compound <b>3</b> belongs to a new class of pyran-opyrans that possess anti-bacterial and phytotoxic activity. Crys  ...[more]

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