113606-75-0Relevant academic research and scientific papers
Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: A new-type azafulvenium reactivity of indole
Kilic,Bayindir,Erdogan,Agopcan Cinar,Konuklar,Bali,Saracoglu,Aviyente
, p. 9674 - 9687 (2017/09/18)
The indole nucleus is a privileged heterocyclic scaffold, which is present in several natural and synthetic compounds. New synthetic strategies to access functionalized indoles have therefore attracted the attention of both synthetic and medicinal chemists over the decades. In this study, the bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles and 1,3-di(1H-indol-3-yl)benzene derivatives is reported for the first time. Using 3-methylindole with cyclopentanone, cyclohexanone, and cycloheptanone results in new and different synthetic pathways. The plausible reaction mechanisms are presented and supported with DFT (M06-2X/6-31+G(d,p)) calculations.
Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
Zhou, Shuguang,Wang, Jinhu,Wang, Lili,Chen, Kehao,Song, Chao,Zhu, Jin
supporting information, p. 3806 - 3809 (2016/08/16)
A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.
Reactions of Dimethyl Acetylenedicarboxylate with Indoles having Bulky 3-Substituents, and Further Reactions of Pyrroloindoles
Letcher, Roy M.,Choi, Michael C. K.,Wai, John S. M.
, p. 2629 - 2659 (2007/10/02)
The addition of dimethyl acetylenedicarboxylate to nine pyrroloindoles, and to nine N-methylindoles with bulky 3-substituents, has yielded twenty three new adducts.Their structures, elucidated mainly from spectroscopy which includes extensive diagnostic use of 13C-1H n.m.r. coupling constants, show several novel features, but all adducts are related to known adduct types.The results show that for relatively unstrained pyrroloindoles, the formation of an amino-ketone intermediate is still significant, but not dominant, that bulky 3-alkyl substituents of indoles can be eliminated to give 2-hydroxycarbazoles, and also that 3-phenyl groups appear to inhibit any reaction.
