Elizaveta D Yakovleva, Evgeniya R Shelukho, Maryana A Nadirova, Pavel P Erokhin, Daria N Simakova, Victor N Khrustalev, Mikhail S Grigoriev, Anton P Novikov, Anna A Romanycheva, Anton A Shetnev, Olga P Bychkova, Alexey S Trenin, Fedor I Zubkov, Vladimir P Zaytsev
Thienylallylamines, readily accessible from the corresponding thienyl aldehydes, react with maleic and trifluoromethylmaleic anhydrides leading to the formation of acids with a thieno[2,3- f ]isoindole core. The reaction sequence involves two successive steps: acylation of the nitrogen atom of the initial allylamine and the intramolecular Diels-Alder vinylarene (IMDAV) reaction. The scope and limitations of the proposed method were thoroughly investigated. It has been revealed with the aid of X-ray analysis and DFT calculations that the key step, the IMDAV reaction, proceeds through an exo -transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle...
March 8, 2024: Organic & Biomolecular Chemistry