303043-76-7Relevant academic research and scientific papers
Oxidative Aza-Annulation of Enynyl Azides to 2-Keto/Formyl-1H-pyrroles
Reddy, Chada Raji,Panda, Sujatarani A.,Ramaraju, Andhavaram
, p. 944 - 949 (2017)
A method for the construction of pyrroles bearing a 2-keto or formyl group through the intramolecular oxidative aza-annulation of enynyl azides is reported for the first time. It involves a sequential carbon-nitrogen/carbon-oxygen bond formations, and the combination of AuCl3 with AgSbF6 was identified as a suitable reagent system to promote the present reaction. The required enynyl azides are readily prepared from Morita-Baylis-Hillman (MBH) acetates of acetylenic aldehydes.
Copper-Catalyzed Intramolecular Chalcogenoamination of Enynyl Azides: Synthesis of 5-Selenyl/Sulfenyl Nicotinates
Reddy, Chada Raji,Ranjan, Ravi,Prajapti, Santosh Kumar
supporting information, p. 623 - 626 (2019/01/21)
A novel methodology for the synthesis of 5-selenyl/sulfenyl nicotinates involving copper-catalyzed organochalcogenyl aza-annulation of enynyl azide with diorganyl-dichalcogenides has been described. This method offers difunctionalization of alkynes via regioselective intramolecular chalcogenoamination in one pot to provide substituted 5-chalcogenyl nicotinates in good to excellent yields. The resulting nicotinates provide access to their oxides, sulfones, and acid derivatives.
Stereoselective synthesis of 2,3-dihydropyrroles from terminal alkynes, azides, and α,β-unsaturated aldehydes via N-sulfonyl-1,2,3-triazoles
Miura, Tomoya,Tanaka, Takamasa,Hiraga, Kentaro,Stewart, Scott G.,Murakami, Masahiro
supporting information, p. 13652 - 13655 (2013/10/01)
A stereoselective method for synthesis of trans-2,3-disubstituted 2,3-dihydropyrroles is reported. N-Sulfonyl-1,2,3-triazoles prepared from terminal alkynes generate α-imino rhodium carbene complexes, which when combined with α,β-unsaturated aldehydes produce trans-2,3- disubstituted dihydropyrroles. The method can be successfully applied to a one-pot process starting from terminal alkynes.
