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Synthesis 2021; 53(07): 1315-1330
DOI: 10.1055/s-0040-1706484
paper

Easy Access to Novel Tetrahydro-1-benzazepine-2-carboxylic Acids and Tetrahydro-1-benzazepines Carrying [a]-Fused Heterocyclic Units from 2-(Allylaryl)glycinates

Sergio Andrés Guerrero
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   eMail: apalma@uis.edu.co
,
Juan E. Ramírez
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   eMail: apalma@uis.edu.co
,
Carlos M. Sanabria
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   eMail: apalma@uis.edu.co
,
Lina M. Acosta
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   eMail: apalma@uis.edu.co
,
Justo Cobo
b   Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain
,
Manuel Nogueras
b   Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain
,
Alirio Palma∗
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   eMail: apalma@uis.edu.co
› InstitutsangabenA.P. would like to thank Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (Grant No. 2496) for financial support.
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Abstract

A concise, efficient, and versatile approach to access novel tetrahydro-1H-benzo[b]azepine-2-carboxylic acids and tricyclic tetra­hydro-1-benzazepines carrying [a]-fused heterocyclic units is reported. The easily accessible 2-(allylaryl)glycinates were used as starting material to synthesize, via the corresponding 1,4-epoxycycloadducts, the required key intermediate benzo[b]azepine-2-carboxylates. Hydrolysis of the latter afforded the targeted benzo[b]azepine-2-carboxylic acids. The key intermediate was also converted into N-2-chloroacetyl derivatives which, in turn, were transformed into the corresponding tricyclic target hexahydrobenzo[f]pyrazino[1,2-a]azepine-1,4-diones by reaction with benzylamine or aminoethanol. The reaction of the common intermediate with hydrazine gave the corresponding intermediate carbohydrazides, which, by reaction with trimethoxymethane, were transformed into another tricyclic target tetrahydrobenzo[f][1,2,4]tri­azino[4,5-a]azepin-4(3H)-ones. Full spectroscopic characterization (IR, HRMS, and 1H and 13C NMR) is also reported for each compound.

Key words

2-(allylaryl)glycinates - intramolecular 1,3-dipolar cyclo­addition - reductive cleavage - cyclocondensation - tricyclic fused-[a]-1-benzazepines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706484.
  • Supporting Information


Publikationsverlauf

Eingereicht: 19. Juli 2020

Angenommen nach Revision: 07. September 2020

Artikel online veröffentlicht:
15. Oktober 2020

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