115724-83-9Relevant academic research and scientific papers
Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: An entry to a new class of duocarmycin analogues
Al-Said, Naim H.,Shawakfeh, Khaled Q.,Abdullah, Wasim N.
, p. 1446 - 1457 (2007/10/03)
Aryl free-radicals generated at the C-7 position of ethyl indole-2-carboxylates bearing N-allyl and propargylic groups triggered intramolecular cyclizations to furnish a new class of Duocarmycin analogues, formal ethyl pyrrolo[3,2,1-ij]quinoline-2-carboxylate derivatives, through the less favorable 6-endo-trig cyclization mode.
Formation of Indoles, Isoquinolines, and Other Fused Pyridines from Azidoacrylates
Henn, Lothar,Hickey, Deirde M. B.,Moody, Christopher J.,Rees, Charles W.
, p. 2189 - 2197 (2007/10/02)
Mild thermal decomposition in boiling toluene or xylene of the azidocinnamates (1) - (6), readily prepared from the corresponding aldehyde and ethyl azidoacetate, gives indoles in good yield when there is an unsubstituted ortho position, and dihydroisoquinolines, and hence isoquinolines, when there is an o-methyl or methylene group.In the presence of iodine, which seems to favour a radical type process, the yield of isoquinoline is increased, and isoquinoline formation can compete with the indole-forming cyclisation to a free ortho-position.Iodine also catalyses primary enamine formation by a hydrogen abstraction process.The thiophene (7) and pyrazole (8) are formed and decomposed similarly to give the corresponding c-fused pyridines (28) and (29).The 2,6-dichloro compound (9) thermolyses to the stable 2H-azirine (32) which isomerises to the nitrile (33) on stronger heating.Yields in these azide decompositions are sometimes high, though they can be variable and the reactions, though easily carried out, can be complex
