biostudies-literatureUnknown8(63)Pis Diez CMA series of novel 1-(<i>N</i>-indolyl)-1,3-butadienes, as (1 : 1) mixtures of the (<i>E</i>) and (<i>Z</i>) dienes, was prepared in one step by base-catalysed isomerization of <i>N</i>-alkylindoles with a terminal butyne chain. The reaction conditions are mild, and in all cases the yields were very high (>90%). The (<i>E</i>) and (<i>Z</i>) dienes were separable by preparative TLC and could be fully characterized. This isomerization proceeded readily in the case of a butynyl chain, but didn't take place with a pentynyl chain. A mechanism was proposed for this reaction, based on previous studies on the isomerization of alkynes in basic media, and a key intermediate that supports the proposed mechanism could be isolated and fully characterized. A theoretical study of the proposed mechanism wRSC advances35998-36006https://www.ebi.ac.uk/biostudies/studies/S-EPMC9088550biostudies-literatureOne-step preparation of novel 1-(<i>N</i>-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(<i>N</i>-indolyl)-naphthoquinones.PMC9088550Casas APis Diez RPis Diez CMPalermo JAFernandez JFDi Venosa GfalseOne-step preparation of novel 1-(<i>N</i>-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(<i>N</i>-indolyl)-naphthoquinones.A series of novel 1-(<i>N</i>-indolyl)-1,3-butadienes, as (1 : 1) mixtures of the (<i>E</i>) and (<i>Z</i>) dienes, was prepared in one step by base-catalysed isomerization of <i>N</i>-alkylindoles with a terminal butyne chain. The reaction conditions are mild, and in all cases the yields were very high (>90%). The (<i>E</i>) and (<i>Z</i>) dienes were separable by preparative TLC and could be fully characterized. This isomerization proceeded readily in the case of a butynyl chain, but didn't take place with a pentynyl chain. A mechanism was proposed for this reaction, based on previous studies on the isomerization of alkynes in basic media, and a key intermediate that supports the proposed mechanism could be isolated and fully characterized. A theoretical study of the proposed mechanism w2018-01-01T00:00:00Z2018 Oct2025-04-04T21:32:24.508Z2025-04-04T21:32:24.508ZS-EPMC90885503555844110.1039/c8ra05208e