Synthesis 2012; 44(24): 3765-3782
DOI: 10.1055/s-0032-1316808
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Novel 2-Alkenyl-2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2-Alkenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols

Lina María Acosta Quintero
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, Bucaramanga, Colombia   Fax: +57(7)6349069   eMail: apalma@uis.edu.co
,
Alirio Palma*
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, Bucaramanga, Colombia   Fax: +57(7)6349069   eMail: apalma@uis.edu.co
,
Manuel Nogueras
b   Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071, Jaén, Spain   Fax: +34(953)211876   eMail: jcobo@ujaen.es
,
Justo Cobo
b   Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071, Jaén, Spain   Fax: +34(953)211876   eMail: jcobo@ujaen.es
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Publikationsverlauf

Received: 13. August 2012

Accepted after revision: 23. Oktober 2012

Publikationsdatum:
08. November 2012 (online)


Abstract

New series of polyfunctionalized 2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols substituted at C2 with 2-methylprop-1-enyl, (E)-styryl, and (E)-pent-1-enyl were synthesized starting from the corresponding N-alkenyl-substituted [prenyl, trans-cinnamyl, (E)-hex-2-enyl] 2-allylanilines by a three-step sequence consisting of selective oxidation of aromatic secondary amines, intramolecular nitrone–olefin 1,3-dipolar cycloaddition, and reductive cleavage. The intramolecular 1,3-dipolar cycloaddition is stereoselective favoring the exo-cycloadducts (ratio exo/endo 2–3:1). The stereochemistry was determined by exhaustive NMR analysis and X-ray diffraction.

Supporting Information

 
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