40137-29-9Relevant articles and documents
Synthesis of Tetrahydroisoquinolines by Visible-Light-Mediated 6- exo -trig Cyclization of α-Aminoalkyl Radicals
Bach, Thorsten,Grübel, Michael,Jandl, Christian
supporting information, p. 1825 - 1829 (2019/09/09)
Starting from the respective tertiary α-silylmethyl amines, the intramolecular cyclization of α-aminoalkyl radicals to Michael acceptors produced tetrahydroisoquinolines. The reaction conditions included the use of 5 molpercent of an iridium photoredox catalyst, dimethylformamide as the solvent, and equimolar amounts of water and cesium carbonate as the additives. 13 substrates were synthesized from ortho -alkylbenzaldehydes in a three-step procedure involving a carbonyl condensation, a radical bromination, and a substitution by a secondary α-silylmethyl amine. After optimization of the photocyclization, the reaction delivered tetrahydroisoquinolines in moderate to high yields (41-83percent). A facial diastereoselectivity (dr ? 80:20) was observed with chiral substrates and a crystal structure provided evidence for the relative configuration of the major diastereoisomer. A catalytic cycle with direct electron transfer to the photoexcited metal catalyst is proposed.
Therapeutic agents useful for treating inflammatory diseases
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, (2008/06/13)
This invention relates to compounds of formula I and pharmaceutically acceptable salts thereof STR1 in which R1, R2 and R3 independently represent hydrogen, halo, alkyl, alkoxy, phenoxy, phenyl, alkoxycarbonyl, --NR13 R14, halogenated alkoxy, halogenated alkyl, benzyloxy, hydroxy, hydroxyalkyl, (C2-6 alkoxycarbonyl)vinyl, --S(O)n R7, carbamoylalkyl, alkoxycarbonylalkyl, --CONR11 R12, or R1 and R2 together with the phenyl ring represent a naphthyl group; R4 and R5 independently represent hydrogen, alkyl, phenyl or together with the carbon atom represent C3-6 cycloalkyl; R6 represents hydrogen, alkyl or ω-hydroxy alkyl; A represents C2-9 alkylene; R8 represents hydrogen, alkyl, halo, alkoxy, hydroxyalkyl, benzyl or phenyl; R9 and R10 independently represent hydrogen, alkyl, halo, alkoxy, phenyl, hydroxyalkyl, alkoxycarbonyl, nitro, --NR30 R31, alkanoyloxyalkyl, or aminomethyl; which are antiinflammatory and antiallergic agents. Compositions containing these compounds and processes to make them are also disclosed.
Transition Metal Catalyzed Grignard Cross-Coupling to Ortho-Halogenated Aryl Imines. An Efficient Synthesis of Ortho-Substituted Aryl Aldehydes
Pridgen, N. Lendon,Snyder, L.,Prol, J.
, p. 1523 - 1526 (2007/10/02)
N-(o-Halogenated benzylidene)cyclohexylamines 2 were successfully reacted with reducing and nonreducing Grignard reagents in a transition metal catalyzed cross-coupling reaction resulting in an efficient single-step synthesis of ortho-substituted benzaldehydes after acidic workup.The dihalogenated benzylidene amines reacted regioselectively at the amine-activated ortho position to yield ortho-substituted halogenated benzaldehydes.
