APPLICATION OF THE SCHWENK-PAPA REACTION FOR THE SYNTHESIS OF VICINALLY SUBSTITUTED BICYCLO[2.2.1]HEPTANES

For the first time, the influence of the structure of vicinally substituted bicyclo [2.2.1] heptanes on the yield of hydrogenation products under the Schwenk-Papa reaction conditions was studied. It has been shown that the Schwenk-Papa reaction allows one-step reduction of multiple bonds of the bicyclic fragment, double bonds of side alkyl substituents, as well as nitro- cyano- and oxime groups with their joint presence. At the same time, carboxyl and amide groups are not reduced under these conditions.

Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis

The title compound, C10H8ClNO5S, which has potential analgesic activity, crystallizes in space group P21/n. The benzothiazine ring system adopts an intermediate form between sofa and twist-boat conformations. The coplanarity of the ester substituent to the bicyclic fragment is stabilized by an O—H...O intramolecular hydrogen bond. In the crystal, hydrogen bonds of type N—H...O(SO2) link the molecules into zigzag chains extending along the b-axis direction. Neighbouring chains are linked by both O—H...Cl and C—H...Cl interactions. A Hirshfeld surface analysis was used to compare different types of intermolecular interactions, giving contributions of O...H/H...O = 42.0%, C...H/H...C = 17.3%, Cl...H/H...Cl = 14.2%, H...H = 11.1%.