Synthesis of morpholinols, morpholines and benzoxazines starting from nitroepoxides
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Título
Synthesis of morpholinols, morpholines and benzoxazines starting from nitroepoxidesAutoría
Tutor/Supervisor
Rodríguez Pastor, SantiagoTutor/Supervisor; Universidad.Departamento
Universitat Jaume I. Departament de Química Inorgànica i OrgànicaFecha de publicación
2016-07-21Editor
Universitat Jaume IResumen
Nitroepoxides are an underdeveloped class
of compounds with wide potential for use in
chemical synthesis.
Nitroepoxides represent strained systems
displaying two highly oxidized vicinal
positions by nature of ... [+]
Nitroepoxides are an underdeveloped class
of compounds with wide potential for use in
chemical synthesis.
Nitroepoxides represent strained systems
displaying two highly oxidized vicinal
positions by nature of their chemical
connectivity and hence are potentially
exploitable as synthons with vicinal
electrophilic centers.
In 1991, Vankar reported the
transformation of nitroepoxides into amino
ketones.1d Nucleophilic attack of the amine
to the β-position of the nitroepoxide
followed by nitrite extrusion affords the
amino ketone. In that work, nitroepoxides are easily
transformed giving 2-hidroxymorpholines
and 2-hidroxybenzoxazines. A properly
reduction of that gives benzoxazines and
morpholines in high diastereoselectivity. These transformations are efficient, provide
access privileged, bioactive structures, and
produce minimal waste. [-]
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Descripción
Treball final de Màster Universitari en Química Aplicada i Farmacològica. Codi: SIM138. Curs acadèmic 2015-2016
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