ChemInform Abstract: REACTION SEQUENCE OF TRIMETHYL‐P‐BENZOQUINONE WITH CYANACETAMIDES

Abstract

Trimethyl‐p‐benzochinon (I) reagiert mit den Cyanacetamiden (II) in Gegenwart von Natriummethylat zu Hydroxy‐oxindolen (III).

Synthesis of 3-Aryl-2-arylamidobenzofurans Based on the Curtius Rearrangement

“…31 A decade later, derivatives of 2-amino-3-carbethoxy-5-hydroxybenzofuran were described such as 10. 32 Recently N-7-azabicyclo-[2.2.1]heptan-2-yl)-2-phenylamidobenzofuran carboxamides 11 and 12 were described for therapeutic use as nicotinic acetylcholine receptor agonists. 33 In the case of 2-alkylamido-and chiral 2-carbamate benzofurans exemplified by 13 and 14, respectively, it is worthwhile mentioning an elegant synthesis from a range of O-anisyl ynamides was described via a Rh(I)-catalyzed demethylation-cyclization (Figure 3).…”

“…At the same time, more functionalized compounds such as 2,6-bis-benzoylamino-benzo[1,2- b ;4,5- b ′]difuran-3,7-dicarboxylic acid diethyl ether 8 and its derivative 9 appeared in the context of the chemistry of color reactions . A decade later, derivatives of 2-amino-3-carbethoxy-5-hydroxybenzofuran were described such as 10 . Recently N -7-azabicyclo[2.2.1]heptan-2-yl)-2-phenylamidobenzofuran carboxamides 11 and 12 were described for therapeutic use as nicotinic acetylcholine receptor agonists .…”

Cyanoacetamides and their thio- and selenocarbonyl analogues as promising reagents for fine organic synthesis

“…99 2,3,6-Trimethylbenzoquinone (59) reacts with cyanoacetamide (1a) in the presence of sodium methoxide yielding 5-hydroxy-4,6,7-trimethyl-3-cyanoindolin-2-one (60). 100,101 Polysubstituted phthalimide 61 has been obtained by condensation of methyl acetylenedicarboxylate with the amide 1a in the presence of Cu 2 (OAc) 4 in dioxane. Cyanoacetamide (1a) has been used as the starting material in the synthesis of dye 62.…”