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Indoles polyfunctionalized, 3-

Metalation of the amidine 87, followed by introduction of 2-methoxyallyl bromide, furnished the intermediate 88, which underwent acid-induced cyclization to the product 89 (Scheme 12), illustrating an interesting approach to polyfunctionalized indoles suitable for further elaboration <20020L1819>. [Pg.280]

Enders et al. [75] developed a synthesis of polyfunctionalized 3-(cyclohex-enylmethyl)-indoles 125 via a quadruple domino Friedel-Crafts-type Michael-Michael-aldol condensation reaction, in 2010. This cascade sequence is initiated by a Friedel-Crafts reaction of indole (126) by an iminium activation mode to the enal, followed sequentially by an enamine- and an iminium-mediated Michael addition. After an intramolecular aldol-condensation, four C-C bonds are formed and the domino product is constructed bearing three contiguous stereogenic centers (Scheme 10.34). [Pg.376]

Regarding the 2-chloroanilines, a general palladium-catalyzed procedure was reported in 2004 by Nazare and co-workers. ° The procedure represents a very efficient method for the synthesis of polyfunctionalized indoles by direct reaction of substituted 2-chloroanilines with cyclic or acyclic ketones (Scheme 2.116). The procedure is simple to carry out and broadly applicable all the desired products were isolated in good yields. [Pg.90]

Relying, as in the previous studies, on the capability of secondary amine catalysts to activate both nucleophile and electrophile, Enders assembled a quadruple domino Friedel-Crafts-type/Michael/Michael/aldol condensation sequence, affording an efficient and direct asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles 172 with moderate to high yields (Scheme 2.55) [82]. [Pg.47]

D. Enders, C. Wang, M. Mukanova, A. Greb, Chem. Commun. 2010, 46, 2447-2449. Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenyhnethyl)-indoles via a quadruple domino Friedel-Crafts-type/Michael/Michaehaldol condensation reaction. [Pg.69]


See other pages where Indoles polyfunctionalized, 3- is mentioned: [Pg.106]    [Pg.106]    [Pg.23]    [Pg.348]    [Pg.400]   
See also in sourсe #XX -- [ Pg.47 ]




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