93391-85-6Relevant academic research and scientific papers
Aryloxymethyl Radical Cyclizations Mimicking Biological C-C Bond Formation to Methoxy Groups
Ahmad-Junan, S. Asiah,Walkington, Andrew J.,Whiting, Donald A.
, p. 2313 - 2320 (2007/10/02)
Attention is drawn to a small group of diverse natural products whose biosynthesis is unusual in involving formation of O-heterocyclic rings by C-C bond formation to aromatic methoxy groups, in net oxidative and non-oxidative processes.It is shown that ar
BIOMIMETIC RADICAL CYCLISATIONS: SYNTHESIS AND BIOSYNTHESIS OF BENZODIHYDRO-PYRANES AND -FURANS
Walkington, Andrew J.,Whiting, Donald A.
, p. 4731 - 4734 (2007/10/02)
Aryloxymethylene radicals generated by decarboxilation of the thiohydroxamate esters derived from acids (8a), (10a), and (12) undergo 6-endo cyclisation yielding (9), (11), and (14) respectively, mimicking the unusual biosynthetic reactions involved in formation of (1), (3), and (4) in nature.
OXYGEN HETEROCYCLES BY SULPHUR YLIDE ANNULATION. THE REACTION OF DIMETHYLSULPHOXONIUM METHYLIDE ON ortho-HYDROXYBENZAL KETONES; A CASE OF ANNULATION LEADING TO A MIXTURE OF UNEXPECTED OXYGEN HETEROCYCLES
Bravo, Pierfrancesco,Fronza, Giovanni,Ticozzi, Calimero
, p. 93 - 102 (2007/10/02)
Mixtures of several oxygen heterocyclic compounds were obtained from the annulation reaction promoted by dimethylsulphoxonium, methylide, 2, on ortho-hyroxybenzal ketones 1a-h, besides the 1,2-disubstituted cyclopropanes produced by the insertion of the methylene on the activated double bond.We isolated four 2,3-dihydrobenzofurans differently substituted on position three, namely 3-(2'-oxoalkyl)-2,3-dihydrobenzofurans, 5, arising by the usual annulation reaction; 3--2,3-dihydrobenzofurans, 8, generated by the insertion of the whole ylide molecule on substrates 1; 3--2,3-dihydrobenzofurans, 10; finally 3--2,3-dihydrobenzofurans, 17, deriving from 1 by insertion of three methylene units.Besides the above-mentioned compounds, we also isolated the 2-(2'-hydroxyphenyl)-3,6-dihydro-6H-pyrans, 15, containing two further methylene units than substrates 1.The complex reactions responsible for the formation of the different products are described.
