General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations

Catalytic Synthesis of N‐(5‐Methylfurfuryl)aniline from Bio‐Derived Carbohydrates

“…have used commercial Pd/C as catalyst and nitrobenzene as amine precursor under hydrogen pressure for N ‐(5‐methylfurfuryl)aniline production with nitrone as a by‐product. N ‐(5‐methylfurfuryl)aniline is an important raw material for some epoxyisoindoles which is a major kind of nitrogen containing heterocyclic compounds and important pharmaceutical intermediates with good biological activities such as antibacterial, anti‐tuberculosis, anti‐tumor, anti‐inflammatories, combat Alzheimer's and so on . In order to explore a possible industrialization road for the synthesis of N ‐(5‐methylfurfuryl)aniline by catalytic conversion of biomass, we designed a two‐step process to first obtain 5‐methylfurfural from fructose, and then direct reductive amination of 5‐methylfurfural with aniline as amine source to reduce by‐products.…”

Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR)

“…The intramolecular Diels-Alder furan (IMDAF) reaction between ,-unsaturated acid anhydrides and hydrogenated heterocycles, containing a furfurylamine moiety, has been studied for a long time (see, for example, Parker & Adamchuk, 1978;Blokzijl et al, 1991;Varlamov et al, 2006;Groenendaal et al, 2008;Nakamura et al, 2011;Zubkov et al, 2011Zubkov et al, , 2012Zubkov et al, , 2014Toze et al, 2015) and used for diastereospecific synthesis of diverse fused-ring systems. It is arguable that the pathway with a simultaneous controlled formation of four or five new stereogenic centers is the best approach to epoxyisoindoles and affords target adducts under mild conditions with satisfactory yields.…”

Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate

“…For intramolecular cycloaddition reactions of ,-unsaturated acid anhydrides to -furylamines (IMDAF reactions), see: Vogel et al (1999); Zubkov et al (2005). For related compounds, see: Zylber et al (1995); Evans et al (1999); Kachkovskyi & Kolodiazhnyi (2007); Kharitonov et al (2009); Aabid et al (2010); Zubkov et al (2010Zubkov et al ( , 2011Zubkov et al ( , 2014; Toze et al (2011); Wang & Li (2012)…”

“…In the last decade our synthetic group has published some effective strategies for the synthesis of 3,6a-epoxyisoindoles annulated with various heterocycles (Zubkov et al 2010(Zubkov et al , 2011(Zubkov et al , 2014Zaytsev, Mikhailova et al 2012;Zaytsev et al 2013). These strategies were based on the intramolecular cycloaddition reaction of α,βunsaturated acid anhydrides to the heterocycles containing an α-furfurylamine fragment (IMDAF reaction) (Vogel et al, 1999;Zubkov et al, 2005).…”