73633-57-5Relevant articles and documents
216. Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6-(Diisopropylamino)-1-azafulvene Derivatives. Novel Synthesis of 5-Mono- and 4,5-Disubstituted 1H-Pyrrole-2-carbaldehydes
Bray, Brian L.,Hess, Petr,Muchowski, Joseph M.,Scheller, Markus E.
, p. 2053 - 2057 (1988)
The first known lithiated 1-azafulvene derivatives were generated by low-temperature halogen/metal interchange, with t-BuLi, from the corresponding brominated 6-diisopropylamino compounds 3b and 12.These Li species reacted with sundry electrophilic reagents to give products which, on the basic hydrolysis, were converted into 5-mono- or 4,5-disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively.
A sustainable catalytic pyrrole synthesis
Michlik, Stefan,Kempe, Rhett
, p. 140 - 144 (2013/08/24)
The pyrrole heterocycle is a prominent chemical motif and is found widely in natural products, drugs, catalysts and advanced materials. Here we introduce a sustainable iridium-catalysed pyrrole synthesis in which secondary alcohols and amino alcohols are deoxygenated and linked selectively via the formation of C-N and C-C bonds. Two equivalents of hydrogen gas are eliminated in the course of the reaction, and alcohols based entirely on renewable resources can be used as starting materials. The catalytic synthesis protocol tolerates a large variety of functional groups, which includes olefins, chlorides, bromides, organometallic moieties, amines and hydroxyl groups. We have developed a catalyst that operates efficiently under mild conditions.
Pd(0)-Catalyzed Conjugate Addition of Benzylzinc Chlorides to α,β-Enones in An Atmosphere of Carbon Monoxide: Preparation of 1,4-Diketones
Yuguchi, Motoki,Tokuda, Masao,Orito, Kazuhiko
, p. 908 - 914 (2007/10/03)
Pd(0)-catalyzed conjugate addition of benzylzine chloride to methyl vinyl ketone in the presence of chlorotrimethylsilane and lithium chloride in an atmosphere of carbon monoxide at room temperature afforded 1-phenyl-2,5-hexanedione monosilyl enol ether. In this catalytic carbonylation, four components are connected in one reaction. Successive acidic workup generated a variety of 1,4-diketones from substituted benzylzine chlorides or related compounds and α,β-enones. Some products were converted to cyclopentenones or five-membered heterocyclic compounds containing an N, O, or S atom.