Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 616-43-3, is researched, SMILESS is CC1=CNC=C1, Molecular C5H7NJournal, Article, Research Support, Non-U.S. Gov’t, Organic Letters called Direct Synthesis of Bipyrroles Using Phenyliodine Bis(trifluoroacetate) with Bromotrimethylsilane, Author is Dohi, Toshifumi; Morimoto, Koji; Maruyama, Akinobu; Kita, Yasuyuki, the main research direction is bipyrrole regioselective preparation; biindole regioselective preparation; regioselective oxidative dimerization pyrrole indole phenyliodonium trifluoroacetate bromotrimethylsilane.Formula: C5H7N.
Bipyrroles and a biindole are prepared regioselectively by oxidative dimerization of pyrroles or indoles with phenyliodine bis(trifluoroacetate) (PIFA) in the presence of bromotrimethylsilane. 3,4-Disubstituted pyrroles and 4,5,6,7-tetrahydroisoindole undergo dimerization to give 2,2′-bipyrroles (or 4,4′,5,5′,6,6′,7,7′-octahydro-1,1′-biisoindole) in 60-78% yields (with respect to PIFA). 3-Substituted-1H-pyrroles undergo regioselective oxidative dimerization with PIFA and bromotrimethylsilane to give 3,4′-disubstituted-2,2′-bipyrroles as the major products in 52-82% yields along with varying amounts of the 3,3′-disubstituted-2,2′-bipyrroles. 3-Methylindole undergoes oxidative dimerization to give 3,3′-dimethyl-2,2′-biindole in 74% yield in addition to 29% of 2-(3-methyl-1-indolyl)-3-methylindoline. While pyrrole undergoes oxidative dimerization with PIFA and bromotrimethylsilane to give only 2,2′-bipyrrole in 78% yield, 1-phenylpyrrole reacts under similar conditions to give 1,1′-diphenyl-2,3′-bipyrrole in 56% yield.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate