Synthesis Of Dipyrrolobenzo[1,2‐a: 2′,1′‐c][1,4]diazepine Scaffold ViaThree‐Component Reaction

Autor: Zinoveva, Anna D., Borisova, Tatiana N., Podchufarova, Valeria A., Novikov, Anton P., Romanycheva, Anna A., Shetnev, Anton A., Titov, Alexander A., Varlamov, Alexey V., Voskressensky, Leonid G.
Zdroj: Asian Journal of Organic Chemistry; May 2024, Vol. 13 Issue: 5
Abstrakt: A three component reaction employing readily available starting materials: 2‐(1‐pyrrolyl)benzylamine, arylglyoxal monohydrates and electron‐deficient alkenes in the synthesis of dipyrrolobenzo[1,2‐a: 2′,1′‐c][1,4]diazepines ‐ previously undescribed system and indolo[2,1‐c]pyrrolo[1,2‐a][1,4]benzodiazepine derivatives have been shown. Domino reactions of pyrrolo[1,2‐a][1,4]benzodiazepines with electron‐deficient alkenes has been proposed as another approach. The applicability of the three‐component reaction for the synthesis of indolizino[8,7‐b]indole derivatives from tryptamine has been studied. The in vitrobiological activity of title compounds has been tested. A series of novel dipyrrolobenzo[1,2‐a: 2′,1′‐c][1,4]diazepine derivatives has been prepared using domino‐reactions of pyrrolo[1,2‐a][1,4]benzodiazepines with electron‐deficient alkenes and viathree component reaction between 2‐(1‐pyrrolyl)benzylamine, arylglyoxal monohydrate and alkenes. Multicomponent approach has been applied in the synthesis of indolizino[8,7‐b]indole derivatives from tryptamine. The developed methods are simple and convenient procedures giving medium and excellent yields, showing a wide functional group tolerance.
Databáze: Supplemental Index