102889-07-6Relevant academic research and scientific papers
Friedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents
Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
, p. 10314 - 10317 (2018)
An effective and clean FC alkylation of indoles and electron-rich arenes with β-nitroalkenes in HFIP was reported. The desired products are formed rapidly in excellent yields under mild conditions without the need for any additional catalysts or reagents. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives.
Rhodium(II)-Catalyzed Regioselective Carbenoid Insertion Reaction of Simple Indoles with N-Sulfonyltriazoles: A Rapid Access to Tryptamine Vinylogues
Huang, Jiapian,Yang, Yi,Chen, Zhiyuan
, p. 201 - 206 (2016)
A synthetically useful 1,3-insertion reaction of a rhodium-carbenoid into the C(sp2)?H bond of simple indole is disclosed, which produces structurally divergent 2-indolylenamides in good to excellent yields and decent chemo- and regioselectivities. The obtained tryptamine vinylogues can be transformed into biologically important tryptamine derivatives or 3,3′-biindoles with ease.
One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides
Rajasekar, Shanmugam,Yadagiri, Dongari,Anbarasan, Pazhamalai
, p. 17079 - 17084 (2015)
A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline.
