74235-56-6Relevant articles and documents
Synthesis of Diverse Pentasubstituted Pyrroles by a Gold(I)-Catalyzed Cascade Rearrangement-Cyclization of Tertiary Enamide
Chen, Sen,Chen, Si,Li, Jiazhu,Li, Wenzhong,Peng, Wei,Shi, Ran,Wang, Xueyuan,Xu, Xin-Ming,Zhang, Xuesi,Zhu, Yan-Ping
, (2022/02/10)
An efficient Au(I)-catalyzed intramolecular cascade reaction of tertiary enamides tethered an alkynyl group has been developed. The process is composed of a propargyl-claisen rearrangement and 5-exo-dig cyclization. This protocol provided a powerful metho
Diverse Reactivity of Diazatitanacyclohexenes: Coupling Reactions of 2 H-Azirines Mediated by Titanium(II)
Desnoyer, Addison N.,See, Xin Yi,Tonks, Ian A.
supporting information, p. 4327 - 4331 (2018/09/25)
2H-Azirines are versatile coupling partners for the synthesis of N-heterocycles. Herein, we present our studies on the reactivity of Cp2Ti(BTMSA) (1; BTMSA = bis(trimethylsilyl)acetylene) with a variety of azirines. In all the cases examined, the initial organometallic products formed are diazatitanacyclohexenes, presumably formed via oxidative addition of Ti(II) into the C-N bond of the azirine to form an azatitanacyclobutene intermediate, followed by C=N insertion of a second equivalent of azirine into the Ti-C bond to form the observed products. Diazatitanacyclohexene 3, bearing phenyl substituents and derived from 2,3-diphenyl-2H-azirine, fragments to form an azabutadiene and nitrile, which is shown to be catalytic in the presence of excess 2,3-diphenyl-2H-azirine. H-substituted complex 8, derived from 3-phenyl-2H-azirine, decomposes via protonolysis of the Cp ligands. In contrast, the methyl-substituted diazatitanacyclohexene 10, derived from 2-methyl-3-phenyl-2H-azirine, is thermally robust. Attempts to trap the putative azatitanacyclobutene intermediate with an alkyne were unsuccessful, resulting instead in the formation of titanacyclopentadiene (12) from coupling of alkyne with BTMSA. Initial reactivity studies found that 10 could be protonolyzed with AcOH to form mixtures of pyrrole and aziridine products, whereas reacting 10 with MeOH results solely in the formation of 2,4-dimethyl-3,5-diphenyl-1H-pyrrole.
Synthesis of multisubstituted 1H-pyrrole: Selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide
Umeda, Rui,Mashino, Tsukasa,Nishiyama, Yutaka
, p. 4395 - 4399 (2014/06/10)
The novel and efficient selenium-catalyzed reductive N-heterocyclization of γ-nitro substituted carbonyl compounds with carbon monoxide has been developed. Various multisubstituted 1H-pyrroles can be easily prepared by this protocol. The one-pot synthesis
Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates
Shindo, Mitsuru,Yoshimura, Yutaka,Hayashi, Maiko,Soejima, Hiroe,Yoshikawa, Takashi,Matsumoto, Kenji,Shishido, Kozo
, p. 1963 - 1966 (2008/02/02)
An efficient synthetic method for the preparation of multisubstituted furans, thiophenes, and pyrroles using ynolates was developed. This novel formal [4 + 1] annulation by C2-C3 and C3-C4 bond formations Includes cycloaddition, cyclization, decarboxylati