Beilstein J. Org. Chem.2015,11, 1360–1366, doi:10.3762/bjoc.11.146
.11.146 Abstract An intramolecular dehydrogenative C–H activation enabled an efficient synthesis of an uracil-annulated β-carbolinone ring system. The reaction is simple, efficient and high yielding (85–92%).
Keywords: β-carbolinones; cyclization; dehydrogenative C–H activation; Pd(OAc)2; uracil
]. For example, SL651498 was documented as a potential drug development candidate in a research program designed to discover subtype-selective GABAA receptor agonists for the treatment of muscle spasms and generalized anxiety disorder [13]. β-Carbolinones such as strychnocarpine, the alkaloid from
Alstonia venenata, and substituted 1-oxo-13-carbolines were also shown to have serotonin-receptor-binding activity (5-HT receptor) [14]. Moreover the natural and synthetic β-carbolines are also known to show anticancer activity against colon and lung cancers, and some β-carbolinones act as biological
Beilstein J. Org. Chem.2012,8, 1730–1746, doi:10.3762/bjoc.8.198
ions in the key step of the total synthesis of ibogamine alkaloids [60].
Palladium-catalyzed cyclization of N-allyl-1H-indole-2-carboxamides 11 is a fruitful procedure to access β-carbolinones 12 or pyrazino[1,2-a]indoles 13 (Scheme 11) [61][62]. The use of PdCl2(MeCN)2 as the catalyst with 1,4
same couple PdCl2(MeCN)2/CuX2 as catalyst and oxidant, respectively. 2-Indolylallylcarboxamides 48 have been found to be suitable substrates to access variously substituted β-carbolinones 49 and 50 through alkenylation/halogenation or alkenylation/esterification processes selectively obtained by
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Graphical Abstract
Scheme 1:
Typical catalytic cycle for Pd(II)-catalyzed alkenylation of indoles.