Bridged azapolycyclic alcohols from intramolecular epoxide ring openings by amides

Abstract

An epoxide ring opening by an intramolecular nucleophilic attack of an amide group was utilized to synthesize 2-azanorbornan-6-ols and 2-azaadamantan-4-ols. The spectral identification of these compounds is described.

Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis

“…This cascade sequence presumably proceeds by reduction of the nitrile, [61] followed by intramolecular epoxide opening by the resulting amine. [62] Of note, the authors observed that this cyclization is the first of its kind and, importantly, forges the [3.3.1] bicyclic moiety contained within the natural products structure. In addition, the opening of the epoxide elegantly provided a secondary alcohol functional group handle that could be used to later install the indole nucleus.…”

An Expedient Synthesis of Novel Derivatives of Pyrido[2,3‐d]pyrimidines Using Magnetically Supported ZrO2 Nanocatalyst

“…Nach Behandlung von 85 mit H 2 und Rhodium auf Aluminiumoxid fand die gewünschte reduktive Cyclisierungskaskade statt, und das tricyclische Amin 87 wurde in 64 % Ausbeute erhalten. Die Kaskadensequenz verläuft vermutlich über die Reduktion des Nitrils61 und anschließende intramolekulare Epoxidöffnung des gebildeten Amins 62. Erwähnenswert ist, dass diese Cyclisierung die erste ihrer Art ist und auf effektive Weise die in der Struktur des Naturstoffs enthaltene [3.3.1]‐bicyclische Einheit aufbaut.…”

Synthesis and reactions of 4-substituted 2-azaadamantanes

“…Infrared spectrum (film) 3025, 2930, 1730, 1460, 1440, 1360, 1220, 1200, 1100, 1020, and 780 cm-1; nmr (CDC18) (TMS) 1.30-2.70 (11 H, m), 3.56 (3 H, s), 5.55 (2 H, m); mass spectrum (70 eV) m/e (rel intensity) 180 (10), 149 (11), 148 (60), 121 (10), 120 (10), 93, (11), 92 (10), 91 (17), 87 (11), 80 (12), 79 (100), 78 (70), 67 (12), 44 (42), 31 (23), 39 (12). ercdo-BicycIo[3.3.1]non-6-ene-3-carboxyhydrazide (4). A solution of 18 g (0.1 mol) of methyl ester 3 in 40 ml of ethanol was heated to reflux with 15 g (0.3 mol) of 99% hydrazine hydrate.…”