Synthesis of tetrazole fused azepanes and quantum chemical topology study on the mechanism of the intramolecular cycloaddition reaction†
M. S.
Pino-Gonzalez, 
*a
A.
Romero-Carrasco,
a
S.
Calvo-Losada,
*b
N.
Oña-Bernal,
a
J. J.
Quirante
b
and
F.
Sarabia
a
*a
A.
Romero-Carrasco,
a
S.
Calvo-Losada,
*b
N.
Oña-Bernal,
a
J. J.
Quirante
b
and
F.
Sarabia
a
Abstract
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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