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New Metal‐Catalyzed Synthesis of Quinoline and Chromene Skeletons
Author(s) -
Deagostino Annamaria,
Farina Vittorio,
Prandi Cristina,
Zavattaro Chiara,
Venturello Paolo
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600230
Subject(s) - chemistry , quinoline , catalysis , alkoxy group , tosyl , metal , coupling reaction , organic chemistry , combinatorial chemistry , alkyl
Alkoxy‐functionalized butadienylboronic esters have been synthesized starting from α,β‐unsaturated acetals and cross‐coupled with both N ‐protected and N ‐unprotected 2‐bromo‐ and 2‐iodoaniline, and with 2‐iodophenol. In particular, N ‐tosyl‐protected dienylanilines can be transformed under mild conditions into quinolines and quinolinones, in the presence of a Pd II catalyst. Moreover, the cross‐coupling reaction between butadienylboronic esters and iodophenol directly affords chromenes that can be successively transformed into chromenones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)