1484-28-2Relevant articles and documents
Regiospecific bromination of 3-methylindoles with N-bromosuccinimide
Zhang, Puwen,Liu, Ruiyan,Cook, James M.
, p. 3103 - 3106 (1995)
The regiospecific bromination of various substituted 3-methylindoles at either C(2) or the C(3) alkyl moiety was accomplished via an electrophilic of free radical bromination process to provide intermediates for indole alkaloid total synthesis. The regiospecificity of the bromination could be controlled by variation of both the substituent and the N(1) protecting group on the indole ring.
Synthetic Routes to Isomeric Imidazoindoles by Regioselective Ring-Opening of Activated Aziridines Followed by Copper-Catalysed C–N Cyclization
Sayyad, Masthanvali,Wani, Imtiyaz Ahmad,Tiwari, Deo Prakash,Ghorai, Manas K.
, p. 2369 - 2378 (2017)
Two new synthetic routes that deliver substituted imidazoindoles in high yields with excellent ee values have been developed. The reactions proceed through ring-opening of activated aziridines with 2,2-dibromovinylanilines or 2-bromoindoles, followed by a Cu-catalysed domino C–N,C–N-cyclization, or a C–N cyclization, respectively. The first route gives rise to one regioisomer, and the second route gives the other.
The synthesis of indolo- and pyrrolo[2,1-a]isoquinolines
De Koning, Charles B.,Michael, Joseph P.,Pathak, Rakhi,Van Otterlo, Willem A.L.
, p. 1117 - 1119 (2007/10/03)
The synthesis of fused isoquinolines from N-benzyl protected indoles and pyrroles is described. For example, treatment of t-butyl-2-(2-formyl-3,4- dihydro-1-naphthalenyl)-3-methyl-1H-indole-1-carboxylate with KOBut in DMF provided 14-methyl-8-phenylbenzo[h]indolo[2,1-a]isoquinoline in good yield. Analogous N-benzylpyrrole precursors could similarly be cyclized to give pyrrolo[2,1-a]isoquinolines.
