Development and applications of amino acid-derived chiral acylnitroso hetero Diels-Alder reactions

Tautomerization of 2-nitroso-N-arylanilines by coordination as N,N′-chelate ligands to rhenium(i) complexes and the anticancer activity of newly synthesized oximine rhenium(i) complexes against human melanoma and leukemia cells in vitro☆

“…Single crystals were obtained by slow sublimation at 55°C and 1.0× 10 − 3 mbar. The structure analysis revealed two planar aromatic rings (C(1)-C(6) and C(7)-C (12)) whereas the first ring shows some quinoid contribution. C-C bond lengths for C(3)−C(4) and C(5)-C(6) are noticeable shortened in comparison to the remaining aromatic ring.…”

“…Its relevance in organic chemistry [7] was first proved 1899 by the Ehrlich-Sachs reaction [8]. Examples published in recent years are application in ene reactions [9] or hetero Diels-Alder reactions [10][11][12]. The discovery of the important roles of C-nitroso compounds in various biological metabolic processes [13][14][15][16][17][18][19][20][21] has also generated a renewed interest in this class of compounds.…”

5.10 Hetero-Diels–Alder Reactions

“…[97][98][99][100] The nitroso Diels-Alder reaction between compounds 193 and unactivated dienes gives 3,6-dihydro-1,2-oxazines 194, which could serve as 1-amino-4-hydroxy-2-ene derivatives, in a single step (equation 23). This section summarizes recent advancements in diastereo-and enantioselective nitroso Diels-Alder reactions.…”

Hetero‐Diels‐Alder‐Reaktionen von Nitrosocarbonylverbindungen als nützliches Verfahren in der organischen Synthese

“…[4] Elektronenziehende Gruppen am aromatischen Ring beschleunigen die Reaktion in hohem Maß. [17] ¾hnliche Effekte wurden für in a-Position substituierte Nitrosoalkane beobachtet, zum Beispiel für die Chlornitrosospezies 5 [19][20][21] und die Acetoxynitrosospezies 6.…”