Heck reaction on protected 3-alkyl-1,2-dien-1-ols: an approach to substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines.
A phosphine-free annulation reaction has been exploited for the preparation of substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines in good to excellent yields. This has been done by reaction of protected 3-alkyl-1,2-dienols with o-iodophenols or protected o-iodoanilines. Two different heterocyclic skeletons were obtained, depending on the electron-donating properties of the heteroatom involved in the annulation process.
Boi
Tommaso
T
Dipartimento di Chimica Generale e Chimica Organica, Università degli studi di Torino, Via Pietro Giuria, 7, 10125 Torino, Italy.
Deagostino
Annamaria
A
Prandi
Cristina
C
Tabasso
Silvia
S
Toppino
Antonio
A
Venturello
Paolo
P
D000438:Alcohols / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D001572:Benzofurans; D007211:Indoles