{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["8(63)"],"submitter":["Pis Diez CM"],"pubmed_abstract":["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 w"],"journal":["RSC advances"],"pagination":["35998-36006"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9088550"],"repository":["biostudies-literature"],"pubmed_title":["One-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."],"pmcid":["PMC9088550"],"pubmed_authors":["Casas A","Pis Diez R","Pis Diez CM","Palermo JA","Fernandez JF","Di Venosa G"],"additional_accession":[]},"is_claimable":false,"name":"One-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.","description":"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 w","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018 Oct","modification":"2025-04-04T21:32:24.508Z","creation":"2025-04-04T21:32:24.508Z"},"accession":"S-EPMC9088550","cross_references":{"pubmed":["35558441"],"doi":["10.1039/c8ra05208e"]}}