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.
|Titolo:||6-chloro-spirocyclohexenindol-2-ones: An unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates|
BECCALLI, EGLE MARIA (Primo)
CLERICI, FRANCESCA (Secondo)
GELMI, MARIA LUISA (Ultimo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||1999|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/S0040-4020(99)00475-5|
|Appare nelle tipologie:||01 - Articolo su periodico|