Download PDF
Synthesis 1993; 1993(1): 152-157
DOI: 10.1055/s-1993-25821
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Formation of New Heterotetracyclic Compounds by Ring Closure of 2-Amino-3-vinylpyridines

Vicente Ojea* , Carlos Peinador, Juan Vilar, José M. Quintela
  • *Departamento de Química Fundamental e Industrial, Facultad de Ciencias, Universidad de La Coruña, E-15071 La Coruña, Spain
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

2-(Isoindol-2-yl)- and 2-(isoquinolin-2-yl)-3-(2,2-dicyanovinyl)pyridine derivatives react thermally in polar solvents via [1,5]hydrogen transfer followed by carbon-carbon bond formation to give 1,5b,6,7-tetrahydroisoindolo[2,1-a][1,8]naphthyridine-6,6, 9-tricarbonitrile and 2,6b,7,8-tetrahydro-1H-isoquino [2,1-a][1,8]naphthyridine-7,7,10-tricarbonitrile derivatives, respectively. The corresponding 2-(indol-1-yl)- and 2-(quinolin-1-yl)-3-(2,2-dicyanovinyl) pyridine derivatives lend themselves more readily to thermal electrocyclic ring closure followed by aromatization to give 2, 6-dihydro-1H-indolo[1,8,7-a,b][1,8]naphthyridine and 1,2,3,7-tetrahydroquino[1,9,8-a,b][1,8]naphthyridine derivatives. Thus, new heterotetracyclic compounds containing the 1,8-naphthyridine group were svnthesized in both ways.