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Synthesis of 5‐Carbapterocarpens by α‐Arylation of Tetralones Followed by One‐Pot Demethylation/Cyclization with BBr 3
Author(s) -
Fernandes Talita de A.,
Domingos Jorge L. O.,
da Rocha Luiza I. A.,
de Medeiros Sabrina,
Nájera Carmen,
Costa Paulo R. R.
Publication year - 2014
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.201301505
Subject(s) - chemistry , tetralones , demethylation , microwave irradiation , catalysis , medicinal chemistry , organic chemistry , stereochemistry , biochemistry , gene expression , dna methylation , gene
Abstract 5‐Carbapterocarpens, one of them displaying estrogenic activity, were prepared from α‐aryltetralones in high yields through a one‐pot, BBr 3 ‐promoted O ‐demethylation and cyclization sequence. The key α‐aryltetralone intermediates were obtained by direct α‐arylation of tetralones with o ‐alkoxybromoarenes in the presence of Pd 2 (dba) 3 (2.5 mol‐%) and t Bu 3 PHBF 4 (10 mol‐%) as catalysts, together with 2.5 equiv. of KOH in dioxane/H 2 O (4:1), under microwave irradiation conditions (80 W, 100 °C, 40 min), leading to α‐monoaryltetralones in good yields.