138691-41-5Relevant academic research and scientific papers
Vinylic MIDA boronates: New building blocks for the synthesis of aza-heterocycles
Llona-Minguez, Sabin,Desroses, Matthieu,Ghassemian, Artin,Jacques, Sylvain A.,Eriksson, Lars,Isacksson, Rebecka,Koolmeister, Tobias,Stenmark, P?l,Scobie, Martin,Helleday, Thomas
, p. 7394 - 7398 (2015)
Abstract A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif. Old dog, new tricks: A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.
Reactivity of Nitro- and Nitroso-arenes with Vinyl Grignard Reagents: Synthesis of 2-(Trimethylsilyl)indoles
Bartoli, Giuseppe,Bosco, Marcella,Dalpozzo, Renato,Palmieri, Gianni,Marcantoni, Enrico
, p. 2757 - 2762 (2007/10/02)
The reaction of nitrosoarenes and 1-(trimethylsilyl)vinylmagnesium bromide in dibutyl ether represents a useful tool for the synthesis of 2-(trimethylsilyl)indoles by cyclisation of benzene derivatives.The use of more common ethers as the solvent leads to large amounts of azo and azoxy derivatives.Conversely, the reaction of nitroarenes and 1-(trimethylsilyl)vinylmagnesium bromide gives conjugate addition products.The reasons for this behaviour are discussed.
