14073-26-8Relevant articles and documents
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.
THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 8. THE PAAL-KNORR REACTION WITH CYCLIC 2-(ACYLMETHYL)-2-ALKYL-1,3-DIKETONES: ISOLATION OF 1-ACYL-1H-PYRROLES VIA REARRANGEMENT
Maini, Prem Nath,Sammes, Michael P.,Katritzky, Alan R.
, p. 161 - 168 (2007/10/02)
Treatment of cyclic 2-acylmethyl-2-alkyl-1,3-diketones with ammonium acetate under reflux in acetic acid gives moderate to high yields of 1-acyl-1H-pyrroles by rearrangement.Some of the cyclic diketones react quantitatively with liquid ammonia to yield 2-