Substituted β-phenylethylamides undergo smooth intramolecular cyclization to 3,4-dihydroisoquinolines in good to excellent yields when treated with bromotriphenoxyphosphonium bromide at –60 °C in dichloromethane in the presence of triethylamine. The reaction proceeds under the mildest conditions ever reported for Bischler–Napieralski-type cyclizations. When chlorotriphenoxyphosphonium choride is used, low yields are obtained instead.
A very mild access to 3,4-dihydroisoquinolines using triphenyl phosphite-bromine-mediated Bischler-Napieralski-type cyclization / Vaccari, Daniele; Davoli, Paolo; Ori, Claudia; Spaggiari, Alberto; Prati, Fabio. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 18:18(2008), pp. 2807-2810. [10.1055/s-0028-1083544]
A very mild access to 3,4-dihydroisoquinolines using triphenyl phosphite-bromine-mediated Bischler-Napieralski-type cyclization
VACCARI, Daniele;DAVOLI, Paolo;ORI, CLAUDIA;SPAGGIARI, Alberto;PRATI, Fabio
2008
Abstract
Substituted β-phenylethylamides undergo smooth intramolecular cyclization to 3,4-dihydroisoquinolines in good to excellent yields when treated with bromotriphenoxyphosphonium bromide at –60 °C in dichloromethane in the presence of triethylamine. The reaction proceeds under the mildest conditions ever reported for Bischler–Napieralski-type cyclizations. When chlorotriphenoxyphosphonium choride is used, low yields are obtained instead.
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