90642-57-2Relevant articles and documents
Sequential Addition/Elimination/Annulation Reactions of 4-Pentynones with Benzylamine and Ammonia
Arcadi, Antonio,Rossi, Elisabetta
, p. 667 - 668 (1997)
The sequential addition/elimination/cycloammination of 4-pentynones in the presence of benzylamine or ammonia produces 1,2,3,-5-substituted and 2,3,5-substituted pyrroles and fused pyrrole sytems, respectively in good to high yields. The methodology has been extended to the preparation of the 17β-hydroxyandrost-4-ene[3,2-b](1-benzyl-5-methyl)pyrrole.
Palladium-catalyzed amino-heck reaction of γ,δ-unsaturated ketone O-diethylphosphinyloximes: A new synthesis of substituted pyrroles and indoles
Zhu, Jia-Liang,Chan, Yu-Hui
scheme or table, p. 1250 - 1254 (2009/04/06)
γ,δ-Unsaturated ketone O-diethylphosphinyloximes, readily prepared from the corresponding ketones, were used as starting materials for the intramolecular amino-Heck reactions. In the presence of a catalytic amount of Pd(PPh3)4 in DBU, cyclization reactions occurred preferentially via a 5-exo fashion to afford a variety of 2-substituted 5-methyl-1H-pyrroles and several indole derivatives in moderate to high yields. Georg Thieme Verlag Stuttgart.
Nitrogen fixation: Synthesis of heterocycles using molecular nitrogen as a nitrogen source
Mori, Miwako,Akashi, Masaya,Hori, Masanori,Hori, Katsutoshi,Nishida, Mayumi,Sato, Yoshihiro
, p. 1655 - 1670 (2007/10/03)
Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium-nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(O iPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium-nitrogen complexes. Although the structures of the titanium-nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.
