RESUMEN
This work reports an efficient synthesis of novel benzo[7,8]indolizino[2,3,4,5-ija]quinazoline derivatives between 2-(2-ethynylaryl)acetonitriles 1 and anthranils 2. The synthetic approach involves the initial formation of 7-formylindole intermediates that can be implemented by DBU to activate a novel indole-nitrile-aldehyde cyclization.
RESUMEN
Two distinct reaction chemoselectivities were reported for the reactions of α-aryldiazo ketone with 1,3-diphenylcyclopentadiene using gold catalyst and phosphine additives, respectively. In the presence of gold catalyst, α-aryldiazo ketone forms gold carbenes initially that are trapped with this 1,3-disubstituted cyclopentadiene to afford C-H insertion products. In the presence of P(C6F5)3 additive, α-aryldiazo ketone forms diarylketenes initially at elevated temperature, which are further stabilized by P(C6F5)3 to secure their entity before proceeding to unprecedented [4C + 2C] cycloadditions.
RESUMEN
Two catalytic annulations of non-symmetric diarylketenes with thioalkynes are described using gold and phosphine catalysts respectively. We employed α-aryldiazo ketones to generate gold-π-ketenes, ultimately yielding azulen-1-one derivatives. With the same reactants, we utilized P(C6F5)3 to increase the yields of 1-naphthols, notably with a complete regioselectivity.
RESUMEN
This work reports a gold-catalyzed stereoselective synthesis of highly substituted E-configured 2,3-diaza-1,3,5-hexatrienes using α-diazo nitriles and cyclopropene derivatives; such products arise from an atypical diazo attack of α-aryldiazo nitriles at vinylgold carbenes. For these 2,3-diaza-1,3,5-hexatrienes, we develop a novel anionic cyclization of derivatives of one family to form 1H-pyrazolo[4,3-b]pyridine-5-ones.