Synthesis of tetrazole fused azepanes and quantum chemical topology study on the mechanism of the intramolecular cycloaddition reaction
2017
Pino-Gonzalez, M. S. | Romero-Carrasco, A. | Calvo-Losada, S. | Oña-Bernal, N. | Quirante, J. J. | Sarabia, F.
The synthesis of novel tetrazolo azepanes from azido nitriles by 1,3 intramolecular dipolar cycloaddition starting from monosaccharide derivatives is described. A quantum chemical topological study on the intramolecular cyclization process has been conducted rendering a pseudo-concerted mechanism. Conformational study was done for the final products which showed a preferential twist boat conformation, theoretically suitable for mannosidase inhibition. However, the tetrazoles showed no significant inhibition of glycosidases.
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