495-58-9Relevant academic research and scientific papers
Reaction of deoxyvasicinone with organolithium compounds
Shakhidoyatov,Ibragimov,Mukhamedov
, p. 598 - 599 (2010)
4-Butyl-4-hydroxydeoxypeganine was prepared by lithiation of deoxyvasicinone. Deoxypeganine and 1,2-dihydrodeoxypeganine were produced by reduction of deoxyvasicinone with lithium aluminum hydride.
Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis
, p. 9347 - 9360 (2020/08/14)
A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.
Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine
Richers, Matthew T.,Deb, Indubhusan,Platonova, Alena Yu.,Zhang, Chen,Seidel, Daniel
, p. 1730 - 1748 (2013/07/26)
Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues. Georg Thieme Verlag Stuttgart. New York.
Metal-free α-amination of secondary amines: Computational and experimental evidence for azaquinone methide and azomethine ylide intermediates
Dieckmann, Arne,Richers, Matthew T.,Platonova, Alena Yu.,Zhang, Chen,Seidel, Daniel,Houk
, p. 4132 - 4144 (2013/06/04)
We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free α-amination of secondary amines. Calculations predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that iminium ions are unlikely to participate in these transformations. These results were confirmed by experimental deuterium-labeling studies and the successful trapping of the postulated azomethine ylide and azaquinone methide intermediates. In addition, computed barrier heights for the rate-limiting step correlate qualitatively with experimental findings.
α-amination of nitrogen heterocycles: Ring-fused aminals
Zhang, Chen,De, Chandra Kanta,Mal, Rudrajit,Seidel, Daniel
, p. 416 - 417 (2008/09/20)
Aromatic aminoaldehydes react with cyclic amines to produce ring-fused aminals under thermal conditions. This process is applied to two-step syntheses of the quinazolinone alkaloids deoxyvasicinone and rutaecarpine. Copyright
Ring-fused aminals: catalyst and solvent-free microwave-assisted α-amination of nitrogen heterocycles
Polshettiwar, Vivek,Varma, Rajender S.
experimental part, p. 7165 - 7167 (2009/04/10)
A high-yield synthesis of ring-fused aminals via microwave (MW)-assisted α-amination of nitrogen heterocycles at 130 °C under solvent- and catalyst-free conditions is described.
The Stereochemistry of Organometallic Compounds. XLII. The Preparation of Quinazolines Involving Rhodium-Catalysed Hydroformylation of 2-Amino-N-alkenylbenzylamines
Campi, Eva M.,Habsuda, Jana,Jackson, W. Roy,Jonasson, Catrin A. M.,McCubbin, Quentin J.
, p. 2023 - 2034 (2007/10/02)
Rhodium-catalysed reactions of 2-amino-N-alkenylbenzylamines with H2/CO give hexahydropyrrolo- and hexahydropyridoquinazolines.Reactions of N-allyl derivatives give a single regioisomer, and reactions of but-3-enyl analogues give mixtures of pyrrol
