The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chlorospirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiane the spiro compounds 3 f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8.

6-chloro-spirocyclohexenindol-2-ones: An unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates / E.M. Beccalli, F. Clerici, M.L. Gelmi. - In: TETRAHEDRON. - ISSN 0040-4020. - 55:28(1999), pp. 8579-8586.

6-chloro-spirocyclohexenindol-2-ones: An unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates

E.M. Beccalli
Primo
;
F. Clerici
Secondo
;
M.L. Gelmi
Ultimo
1999

Abstract

The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chlorospirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiane the spiro compounds 3 f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/182113
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 12
social impact