1044518-07-1Relevant articles and documents
Isoindolo[2,1-a]indol-6-one-a new pyrolytic synthesis and some unexpected chemical properties
Crawford, Lynne A.,Clemence, Nathan C.,McNab, Hamish,Tyas, Richard G.
, p. 2334 - 2339 (2008)
Isoindolo[2,1-a]indol-6-one 1 is formed by a sigmatropic shift-elimination-cyclisation cascade by flash vacuum pyrolysis (FVP) of methyl 2-(indol-1-yl)benzoate 7 at 950 °C. The dihydro compound 16 is easily obtained by catalytic reduction of 1, but the reaction is very sensitive to steric effects at the 11-position. Attempted ring-opening of 1 in basic methanol provides an equilibrium of isoindolo[2,1-a]indol-6-one 1 and the ester 19. Lithium aluminium hydride reduction of 1 provides the alcohol 22 which can be dehydrated to a mixture of 23 and 24 by FVP at 800-950 °C.
An expedient synthesis of indolo[1,2-a]quinolines via Mn(OAc)3-mediated oxidative free radical cyclization and NaI/O2-assisted dealkoxycarbonylation/ aerobic oxidation cascade
Lee, Hyun Seung,Kim, Se Hee,Kim, Yu Mi,Kim, Jae Nyoung
scheme or table, p. 5071 - 5075 (2011/01/04)
An expedient synthetic procedure of indolo[1,2-a]quinolines was developed using a sequential Cu-mediated N-arylation of indole, Mn(OAc) 3-mediated oxidative free radical cyclization, and NaI/O 2-assisted concomitant dealkoxycarbonylation/aerobic oxidation. The last step was replaced by a palladium-catalyzed decarboxylation/elimination protocol for the allyl ester derivatives.
Thermal Ring Contraction of Dibenz[b,f]azepin-5-yl Radicals: New Routes to Pyrrolo[3,2,1-jk]carbazoles
Crawford, Lynne A.,McNab, Hamish,Mount, Andrew R.,Wharton, Stuart I.
, p. 6642 - 6646 (2008/12/22)
(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of N-allyl- or N-benzyldibenz[b,f]azepine at temperatures from 750 to 950°C gives pyrrolo[3,2,1-jk]carbazole as the major product. The mechanism of the ring contraction involves dibenzazepin-1-yl radical formation, followed by transannular attack and formation of a 2-(indol-1-yl)phenyl radical which cyclizes. The mechanism is supported by independent generation of 2-(indol-1-yl)phenyl radicals by two different methods, and the use of 1-(2-nitrophenyl)indole as a radical generator gives an optimized synthetic route to pyrrolo[3,2,1-jk]carbazole (54% overall yield in two steps from indole). The first substituted pyrrolo[3,2,1-jk]carbazoles have been synthesized by FVP methods and also by reactions of the parent compound with electrophiles, leading to a range of 4-substituted pyrrolocarbazoles.