- Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles
-
Anilines react with alkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180°C in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2·2H2O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2·2H2O is necessary for the effective formation of indoles. A reaction pathway involving alkanol group transfer from alkanolamines to anilines, N-alkylation of anilines by anilinoalkanols and heteroannulation of 1,2-dianilinoalkanes is proposed for this catalytic process.
- Cho, Chan Sik,Kim, Jin Hwang,Kim, Tae-Jeong,Shim, Sang Chul
-
p. 3321 - 3329
(2007/10/03)
-
- A Stereochemical Investigation of 1,3-Diphenyl-4-methyl-1,3-diazolidines and its Related Compounds via NMR
-
Four 1,3-diphenyl-4-methyl-1,3-diazolidines and two isomeric 2,5-diphenyl-3-methyl-1,2,5-thiadiazolidine 2-oxides were prepared.The pmr and cmr spectra of these compounds were obtained.On the basis of the chemical shifts due to the γ- and δ-effects, the stereochemical structures are discussed.
- Nishiyama, Tomihiro,Nanno, Yukio,Yamada, Fukiko
-
p. 1773 - 1776
(2007/10/02)
-
- β-Substituted Organoalkaline Tri- and Tetra-anions; Preparation, Stability, and Reactivity
-
New β,γ-, β,β'-disubstituted organometallic trianions of the type C(Y)C(Y')C(8) and C(Y)CC(Y') (18) (Y = or (*) Y' = O, PhN), β-substituted organodimetallic trianions of the type CC(PhN)C (25) with alkali-metal cations (Li, Na, and K), and a lithiated tetra-anion of the type CC(PhN)C(PhN)C (32) are obtained from the corresponding substituted organomercury(II) compounds via low-temperature mercury-alkali metal transmetallation.The starting organomercurials can be obtained by solvomercuriation from suitable unsaturated systems.These polyanion derivatives are stable species only at temperatures in the range -78 to -100 deg C; at higher temperatures rapid decomposition takes place via either a β-elimination process or proton abstraction from the reaction media.The new polyanionic compounds are characterized by transformation into their deuterio derivatives with deuterium oxide at low temperature.The thermal decomposition of these organometallic intermediates is also reported.The reactivity of the lithiated trianion derived from isopropylaniline (25a) with different agents (ethyl bromide, dimethyl disulphide, and trimethylchlorosilane) in a successive or simultaneous way is studied; this process occurs in a regioselective manner.
- Barluenga, Jose,Fananas, Francisco J.,Villamana, Jorge,Yus, Miguel
-
p. 2685 - 2692
(2007/10/02)
-