A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc)(2)-[Cp*RhCl(2)](2) bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.
A method for the synthesis of oxymethyl dihydropyrroles (pyrrolines) and dihydroimidazoles has been developed via Cu(II)-mediated intramolecular aminooxygenation of alkenylimines and alkenylamidines, respectively, with 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO).
a-Azido carbonyl compounds bearing a 2-alkenylaryl moiety in the a-position are found to be promising precursors in the synthesis of isoindoles via 1,3-dipolar cycloaddition of azides to alkenes. Applications of these isoindoles in the preparation of 1,2,3,4-tetrasubstituted naphthalene and 9,10-disubstituted anthracene derivatives were developed via [4+2]-cycloaddition reactions of isoindoles with dimethyl acetylenedicarboxylate and benzynes, respectively, followed by deaminative aromatization.
Cu(II)-Mediated Aminooxygenation of Alkenylimines and Alkenylamidines with TEMPO. -The process allows the preparation of dihydropyrrole and dihydroimidazole units bearing an oxymethyl function. -(SANJAYA, S.; CHUA, S. H.; CHIBA*, S.; Synlett 2012, 11, 1657-1661, http://dx.
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