1403612-08-7Relevant academic research and scientific papers
Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives
Hussain, Mulla Althafh,Khan, Faiz Ahmed
supporting information, (2019/08/20)
A full account of the total synthesis of aspidostomide B, C, their analogues and our synthetic efforts towards the synthesis of aspidostomide D, which led to the synthesis of regioisomeric N-methyl aspidostomide D, its analogues via epoxide opening strategy is presented. The synthesis of regioisomeric N-methyl aspidostomide D involves an efficient, five-step sequence, with 36.3% overall yield, starting from 3,4,5-tribromo-1H-pyrrole-2-carboxylic acid. The key features of this protocol are intramolecular cyclization, dehydration, oxidation, and a Lewis acid-mediated regioselective epoxide ring opening by C-3 position of 2,5-dibromo-1H-indole to furnish the title compounds.
Formal [4+ 2] reaction between 1,3-diynes and pyrroles: Gold(I)-catalyzed indole synthesis by double hydroarylation
Matsuda, Yuka,Naoe, Saori,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
supporting information, p. 1463 - 1467 (2015/01/30)
Indole synthesis by a gold(I)-catalyzed intermolecular formal [4+2] reaction between 1,3-diynes and pyrroles has been developed. This reaction involves the hydroarylation of 1,3-diynes with pyrroles followed by an intramolecular hydroarylation to give the 4,7-disubstituted indoles. This reaction can also be applied to the synthesis of carbazoles when indoles are used as the nucleophiles instead of pyrroles.
Fused arene ring construction around pyrrole to form 4,7-disubstitued indole
Nojman,Latos-Grazynski,Szterenberg
experimental part, p. 4115 - 4122 (2012/10/08)
A method for synthesizing 4,7-diarylindoles and 4,7-di(thien-2-yl)indole by applying a strategy where the fused benzene ring was built on an existing pyrrole in an acid-catalyzed rearrangement of 1,4-diaryl-1,4-di(pyrrol-2-yl)but- 2-yne and 1,4-di(pyrrol-2-yl)-1,4-di(thien-2-yl)but-2-yne, respectively, is presented. In the presence of TFA (30 equiv.), 4,7-diarylindoles undergo thermodynamically equilibrated dimerization at 240 K as determined by 1H NMR spectroscopy and substantiated by DFT calculations. An alternative route for the construction of indole derivatives is described. 4,7-Diarylindoles and 4,7-di(thien-2-yl)indole were synthesized by applying a strategy where the fused benzene ring was built on the existing pyrrole.
