Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: unexpected formation of glycosazones.
The present contribution discloses a simple and unexpected acid-catalyzed cleavage of tetrahydrotetrazines leading to 1,2-bis(hydrazones). Incorporation of a chiral fragment derived from carbohydrates enables the rapid preparation of glycosazones, a family of compounds employed by Emil Fischer to elucidate the configuration of sugars. In addition, a mechanistic proposal accounts for experimental observations.
Avalos
Martín
M
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura, E-06071 Badajoz, Spain.
Babiano
Reyes
R
Cintas
Pedro
P
Clemente
Fernando R
FR
Gordillo
Ruth
R
Hursthouse
Michael B
MB
Jiménez
José L
JL
Light
Mark E
ME
Palacios
Juan C
JC