1439384-41-4Relevant academic research and scientific papers
A base-catalyzed cycloisomerization of 5-cyano-pentyne derivatives: An efficient synthesis of 3-cyano-4,5-dihydro-1H-pyrroles
Meng, Jia,Li, Yi-Jin,Zhao, Yu-Long,Bu, Xiu-Bin,Liu, Qun
, p. 12490 - 12492 (2014)
A base-catalyzed cycloisomerization of 5-cyano-pentyne bearing a terminal alkyne group has been developed under metal-free conditions. This reaction involves a tandem process providing efficient access to 3-cyano-4,5-dihydro-1H-pyrroles in good to excellent yields in an atom-economic manner with 1,3-cyano migration as the key transformation. This journal is
Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds
Eberlin, Ludovic,Carboni, Bertrand,Whiting, Andrew
, p. 6574 - 6583 (2015/10/06)
A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp2 boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp3 boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. 1H and 11B NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition-elimination sequence.
A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds
Tripoteau, Fabien,Eberlin, Ludovic,Fox, Mark A.,Carboni, Bertrand,Whiting, Andrew
supporting information, p. 5414 - 5416 (2013/06/27)
A one-pot hetero-Diels-Alder/ring contraction cascade is presented from the reaction of 1-boronodienes and arylnitroso derivatives to derive N-arylpyrroles in moderate to good yields (up to 82%).
