- Facile synthesis of 2-substituted 4-azaindoles
-
A novel and efficient strategy for the synthesis of 2-substituted 4-azaindoles from 2-chloro-3-nitropyridine through Pd-catalyzed Sonogashira cross-coupling, followed by reduction and heteroannulation on t-BuOK, is reported. Copyright Taylor & Francis Group, LLC.
- Sun, Li-Ping,Wang, Jin-Xin
-
-
Read Online
- A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes
-
An inherently regiospecific synthesis of isatins (1H-indole-2,3-diones) starting from 1-halo-2-nitrobenzenes is described. The isatins are formed by an intramolecular palladium-catalyzed annulation of 2-(2-haloethynyl)-1-nitrobenzenes via the formation of 2-haloisatogens.
- S?derberg, Bj?rn C.G.,Gorugantula, Sobha P.,Howerton, Chet R.,Petersen, Jeffrey L.,Dantale, Shubhada W.
-
experimental part
p. 7357 - 7363
(2009/12/04)
-
- Condensed Heteroaromatic Ring Systems. XII. Synthesis of Indole Derivatives from Ethyl 2-Bromocarbanilates
-
The palladium-catalyzed reaction of ethyl 2-bromocarbanilate with trimethylsilylacetylene yielded ethyl 2-(trimethylsilylethynyl)carbanilate, which was treated with sodium ethoxide to give indole.The carbanilates having a methyl or a bromo substituent were similarly transformed to corresponding indole derivatives.Furthermore, pyrrolo- and Pyrrolopyridines were synthesized by this method.Keywords---palladium-catalyzed reaction; trimethylsilylacetylene; ethyl 2-halocarbanilate; ethyl 2-halopyridinecarbamate; ethyl 2-(trimethylsilylethynyl)carbanylate; ethyl o-(trimethylsilylethynyl)pyridinecarbamate;indole;pyrrolopyridine
- Sakamoto, Takao,Kondo, Yoshinori,Iwashita, Shigeki,Yamanaka, Hiroshi
-
p. 1823 - 1828
(2007/10/02)
-
- Condensed Heteroaromatic Ring Systems. VI. Synthesis of Indoles and Pyrrolopyridines from o-Nitroarylacetylenes
-
Catalytic hydrogenation of o-nitrophenylacetaldehyde diethyl acetal over palladium-carbon, followed by intramolecular cyclization of the resulting o-aminophenylacetaldehyde diethyl acetal with hydrochloric acid, gave indole.Similarly, 4-methylindole, ethyl 5-indolecarboxylate, and various pyrrolopyridines were synthesized from the corresponding o-nitroarylacetaldehyde derivatives.The preparation of the desired o-nitroarylacetaldehydes was accomplished by the condensation of o-halonitroaromatics with trimethylsilylacetylene in the presence of dichloro-bis(triphenylphosphine)palladium as a catalyst, followed by ethanolysis of the resulting o-(trimethylsilylethenyl)nitroaromatics.Keywords - o-halonitroaromatic; o-cyanohaloaromatic; trimethylsilylacetylene; palladium-catalyzed reaction; cyclization; indole; pyrrolopyridine
- Sakamoto, Takao,Kondo, Yoshinori,Yamanaka, Hiroshi
-
p. 2362 - 2368
(2007/10/02)
-