4660-96-2Relevant academic research and scientific papers
I2-induced cascade cyclization and dearomatization of indoles for the highly efficient synthesis of iodinated and vinylic spiroindolenines
Li, Yazhou,Liang, Xuewu,Liu, Hong,Liu, Qi,Liu, Xuyi,Wei, Xiaohui,Zhou, Yu
supporting information, p. 9165 - 9171 (2021/11/23)
The spiroindolenine framework is a privileged heterocyclic motif and is widely present in numerous indole alkaloids. Herein, we develop a metal-free and environmentally friendly approach for the intramolecular cascade cyclization and dearomatization of indole derivatives to selectively afford iodinated and vinylic spiroindolenines by a substrate-controlled strategy. Simple operation, mild conditions, and high yield make this strategy a green and attractive pathway to construct functionalizable spiroindolenine scaffolds, which could be converted into diverse useful spiroindolenine derivatives.
Dearomative Cycloadditions Utilizing an Organic Photosensitizer: An Alternative to Iridium Catalysis
Rolka, Alessa B.,Koenig, Burkhard
supporting information, p. 5035 - 5040 (2020/07/15)
A highly efficient, cheap, and organic alternative to the commonly used iridium photosensitizer (Ir[dF(CF3)ppy]2(dtbpy))PF6 ([Ir-F]) is presented for visible-light energy transfer catalysis. The organic dye 2CzPN surpasses [Ir-F] in selectivity while at t
Visible-light-induced cascade dearomatization cyclization between alkynes and indole-derived bromides: A facile strategy to synthesize spiroindolenines
Gao, Xiaoshuang,Yuan, Yao,Xie, Xiaomin,Zhang, Zhaoguo
supporting information, p. 14047 - 14050 (2020/11/21)
A visible-light-initiated intermolecular dearomatization cyclization cascade reaction between alkynes and indole-derived bromides has been explored. This transformation exhibits a wide substrate scope and significant functional group tolerance, providing an efficient way to access a variety of spiroindolenines under mild conditions. This journal is
Substitution of the Dimethylamino Group in Gramines and One-Pot Cyclization to Tetrahydro-β-carbolines Using a Triazine-Based Activating Agent
Fujita, Hikaru,Nishikawa, Riho,Sasamoto, Ozora,Kitamura, Masanori,Kunishima, Munetaka
, p. 8380 - 8391 (2019/07/08)
A new method for the substitution of 3-[(dimethylamino)methyl]indoles (gramines) with malonate-based nucleophiles was developed using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) as the activating agent for the dimethylamino group. The reaction was completed in 1.5-6 h at room temperature in the presence of a tert-amine base and lithium salt. CDMT afforded superior results to methyl iodide, a common activating agent for the dimethylamino group in Mannich bases, particularly in the reactions of 1-substituted gramines. The reactivity of the possible intermediates, bis(indol-3-ylmethyl)dimethylammonium salts, was examined to obtain mechanistic insights on the reaction. This substitution method with CDMT enabled the sequential transformation of gramines: substitution with (N-alkylidene)aminomalonates followed by the Pictet-Spengler reaction under acidic conditions afforded 1,2,3,4-tetrahydro-β-carboline derivatives in one pot.
A convenient metal-free reagent for the generation and capture of trifluoromethanethiol
Li, Shi-Guang,Zard, Samir Z.
supporting information, p. 5898 - 5901 (2013/12/04)
O-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium O-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with α-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.
PREPARATION AND ARYLATION OF 2-INDOLYLZINC DERIVATIVES
Sakamoto, Takao,Kondo, Yoshinori,Takazawa, Nobuo,Yamanaka, Hiroshi
, p. 941 - 942 (2007/10/02)
2-Arylindoles were synthesized by the palladium catalyzed reaction of aryl halides with 2-indolylzinc derivatives which were derived from the lithio derivatives.
