34132-46-2Relevant academic research and scientific papers
Solvent and catalyst free ring expansion of indoles: A simple synthesis of highly functionalized benzazepines
Bakthadoss, Manickam,Kumar, Polu Vijay,Reddy, Tadiparthi Thirupathi,Sharada, Duddu S.
, p. 8160 - 8168 (2018)
Highly functionalized benzazepines have been synthesized by using various substituted indoles and dialkylacetylene dicarboxylates under thermal and open air conditions. The reaction was carried out in a solvent and under catalyst free conditions and the products are formed in very good yields. The reaction proceeds in a concerted fashion thus providing potentially bioactive benzazepines by ring expansion of a five-membered indole ring. It is also described that the ring contraction of seven-membered benzazepines in the presence of KOtBu base at room temperature smoothly afforded the corresponding 3-alkenylated indole derivatives in very good yields.
Photocycloaddition of Dimethyl Acetylenedicarboxylate to Activated Indoles
Davis, Paul D.,Neckers, Douglas C.
, p. 456 - 462 (2007/10/02)
Photocycloaddition reactions of N-methylindoles to dimethyl acetylenedicarboxylate (DMAD) yield derivatives of cyclobutenes: 9,10-bis(methoxycarbonyl)-2-methyl-3,4-benzo-2-azatricyclodeca-3,9-dienes.No secondary photorearrangements are prevalent, but ring opening of the formed cyclobutenes is effected at moderate temperatures.
