2-Furan methylamine

Sodium and lithium are the most common metals, and diethyl ether, tetrahydro-furan, and HMPA are often used as cosolvents to overcome solubility problems. The Benkeser method,37 204 employing lithium in low-molecular-weight amines (methylamine, ethylamine, ethylenediamine), is a more powerful reducing agent... 

Furan itself can be used as the starting material for the synthesis of 1-methylpyrrole <2002MI179>. 7-AI2O3 was found to be an effective catalyst for the dehydration reaction between furan and methylamine to afford 1-methylpyrrole. A yield of 57.6% was achieved under the experimental conditions of a reaction temperature of 400 °C, a methylamine/ furan molar ratio of 1.5, and the molar flow rate of furan approximately 3-3.5 mmol/h. Furan was adsorbed onto Bronsted acid sites on the catalyst, while the methylamine was adsorbed onto Lewis acid sites. With this heterogeneous catalyst, the rate determining step of the mechanism was suggested to be the adsorption of furan on the Bronsted acid sites to form a ring-opened species, which is followed by the insertion of the adsorbed methylamine to form secondary amine intermediates. Further dehydration at the Lewis acid sites would yield 1-methylpyrrole. 

Wahrend 2-Methyl-furan und Furfurylalkohol mit Lithium/Methylamin lediglich Ge-mische (mit 2-Methylimino-pentan als Hauptprodukt)4 liefert, erhalt man aus 3-Carboxy-furan unter klassischen Birch-Bedingungen in Isopropanol bei nachfolgender Behandlung mit Diazomethan 3-Methoxycarbonyl-2,3-dihydro-furan5 (85% d.Th. Kp30 83 - 84°) ... 

Beginning with furan (15), exposure to bromine in a suspension of potassium carbonate in methanol gave the dimethoxy furan 16. Next, treatment of 16 with potassium permanganate yielded cw-dihydroxylated acetal 17. The acetal functionality was converted to the transient dialdehyde 18, which underwent the title reaction upon exposure to acetonedicarboxylic acid and methylamine under simulated physiological conditions to give teloidinone (19). 

Dimethylaminomethyl) ] furan-5-lmethyl)thio] p amino ethane 1 - (Methylamine) -1- (methylthio)-2-nitroethylene 5-1 - (2-Aminoethyl) -thiomethyl-N,N-dimethyl-2-fiiranmethanamine Tetramisol (3 intermediate)... 

Bromination in methanol leads to 2,5-dimethoxy-2,5-dihydrofuran (3) by trapping the product 1 of a primary 1,4-addition of Br2 to furan by methanolysis. Catalytic hydrogenation of 3 gives 2,5-dimethoxytetrahydrofuran (4), a cycHc bisacetal, which is used in synthesis as a succindialdehyde equivalent. As an example may serve the biomimetic synthesis of tropinone (cf p. 433) from succindialdehyde, methylamine, and acetone dicarboxylic acid (Robinson and Schopf, 1937) [5]. 

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