34560-16-2

Usage

InChI:InChI=1/C6H13NO4/c1-3-10-6(11-4-2)5-7(8)9/h6H,3-5H2,1-2H3

Upstream product

• 51806-20-3 1,1-diethoxy-2-iodoethane 
• 75-52-5 nitromethane 
• 122-51-0 orthoformic acid triethyl ester 
• 1478-41-7 diethoxycarbonium fluoroborate 
• 105-57-7 diethyl acetal 

Downstream Products

• 645-36-3 2,2-diethoxy-ethanamine 
• 129492-41-7 (2R,3S)-2-Benzyloxy-5,5-diethoxy-4-nitro-pentane-1,3-diol 
• 129492-41-7 (2S,3R)-2-Benzyloxy-5,5-diethoxy-4-nitro-pentane-1,3-diol 
• 33884-29-6 5,5-dimethyl-2-nitromethyl-1,3-dioxane 
• 85078-26-8 2-nitro-1,1-di(p-tolyl)ethane 
• 129492-45-1 ((2S,3R)-1-Diethoxymethyl-2,3,4-trihydroxy-butyl)-carbamic acid benzyl ester 
• 129492-45-1 ((2R,3S)-1-Diethoxymethyl-2,3,4-trihydroxy-butyl)-carbamic acid benzyl ester 
• 129492-47-3 Toluene-4-sulfonic acid (2S,3R)-4-amino-5,5-diethoxy-2,3-dihydroxy-pentyl ester 
• 129492-47-3 Toluene-4-sulfonic acid (2R,3S)-4-amino-5,5-diethoxy-2,3-dihydroxy-pentyl ester 
• 129492-46-2 Toluene-4-sulfonic acid (2S,3R)-4-benzyloxycarbonylamino-5,5-diethoxy-2,3-dihydroxy-pentyl ester 
• 129492-46-2 Toluene-4-sulfonic acid (2R,3S)-4-benzyloxycarbonylamino-5,5-diethoxy-2,3-dihydroxy-pentyl ester 
• 129492-49-5 (3S,4R)-2-Diethoxymethyl-pyrrolidine-3,4-diol; compound with toluene-4-sulfonic acid 
• 129492-49-5 (3R,4S)-2-Diethoxymethyl-pyrrolidine-3,4-diol; compound with toluene-4-sulfonic acid 
• 102804-25-1 (Z)-1-dimethylamino-2-nitroethene 

Relevant academic research and scientific papers

Synthesis of 3-nitroindoles by sequential paired electrolysis

3-Nitroindoles are synthetically versatile intermediates but current methods for the preparation hinder their widespread application. Herein, we report that nitroenamines undergo electrochemical cyclisation to 3-nitroindoles in the presence of potassium iodide. Detailed control experiments and cyclic voltammogram studies infer the reaction proceedsviaa sequential paired electrolysis process, beginning with anodic oxidation of iodide (I?) to the iodine radical (I˙), which facilitates cyclisation of the nitroenamine to give a 3-nitroindolinyl radical. Cathodic reduction and protonation generates a 3-nitroindoline that upon oxidation forms the 3-nitroindole.

An alternative isoxazole route to α-alkoxycarbonyl-β-diketones

Cycloaddition of oxygen-functionalized nitrite oxides to the enamine from ethyl acetoacetate produces 4-ethoxycarbonyl-5-methylisoxazoles carrying a 3-tetrahydropyranyloxymethyl, 3-diethoxymethyl or 3-ethoxycarbonyl substituent; the 3-formylisoxazole is prepared from the former two and condensed in situ with phosphoranes to give 3-alkenylisoxazoles that are cleaved by hexacarbonylmolybdenum or hydrogenolysis to afford α-alkoxycarbonyl-β-diketones.