Furfuryl amine

A review concerning the synthesis of optically active a-furfuryl amine derivatives and then-application to asymmetric synthesis appeared <99T11959>. 

Furfuryl amine [617-89-0] M 97.1, b 142.5-143 /735mm, d 1.059, n 1.489. Distd under nitrogen from KOH through a column packed with glass helices. 

Therapeutics. Compounds containing the furan or tetrahydrofuran ring are biologically active and are present in a number of pharmaceutical products. Furfuryl amine [617-89-0] is an intermediate in the diuretic, furosemide. Tetrahydrofurfurylamine [4795-29-3] may also have pharmaceutical applications. 5-(Dimethylaminomethyl)furfuryl alcohol [15433-79-1] is an intermediate in the preparation of ranitidine, which is used for treating ulcers. 

Furosemide, 4-chloro-./V-furfuryl-5-sulfamoyl anthranilic acid, is prepared by treating 2,4,5-trichlorobenzoic acid with chlorosulfonic acid, and further treatment with ammonia and furfuryl amine. 

Furfural Pentose Furfuryl alcohol, furfuryl amine, furan-acrylic acid, tetrahydrofuran, levulinic acid, maleic anhydride Chheda etal., 2007 Corma etal., 2007... 

Formic acid amitrole, chlordimeform, dicofol, fenpropidin, fenpropimorph, fluridone, formothion, metosulam, propiconazole, resmethrin, tricyclazole 2 Furaldehyde furilazole Furan endothal Furfural fuberidazole Furfuryl amine pefurazoate... 

Dichloro-5-sulphamoyl benzoic acid may be prepared by reacting 2,4-dichlorobenzoic acid with chlorosulphonic acid at an elevated temperature and then carrying out the amidation. This on treatment with furfuryl amine in the presence of sodium bicarbonate, affords nueleophilie aromatie displacement of the highly activated chlorine at C-2, thereby yielding furosemide. However, the proteetion of the chlorine atom at C-4 may be achieved by regulating the temperature of the furfuiylamination. 

The piperidine precursor 56 to 1-deoxymannojirimycin is obtained by the kinetic resolution of the a-furfuryl amine derivative using Sharpless epoxidation conditions <97JCS(P1)741>. 

The 3-pyridinols 74 can be prepared from furfural by reductive amination to furfurylamine and oxidation with hydrogen peroxide [135]. The respective 6-hydroxymethyl derivative 75 was prepared from 4-hydroxymethylfurfural by reductive amination followed by exposure to bromine in water/methanol to give a 2,5-dibromo derivative whose hydrolysis, ehmination of water, and cyclization gave 6-hydroxymethyl-3-pyridinol [136]. Similarly, glucosylated furfuryl amine derived from isomaltulose was converted to 76 (Fig. 13). 

The corresponding all-furan polyamides 17-19, obtained with 2,5- and 3,4-bis(furfuryl) amines, were also prepared and characterized but gave disappointing properties particularly in terms of thermal stability because of the lability of the hydrogen atoms in the methylene groups attached to the amine-derived furan rings. 

Transamination is induced by primary amines. It is another important reaction that produces the three corresponding amides, a process discussed below in the context of the coupling of furfuryl amine with epoxidised oils. 

Athy l-f -(4-amino-b zoyloxy ] Athyl ] furfuryl-amin 18 II417. 

The direct conversion into furfuryl alcohol, methylfuran and furan via metal-catalyzed hydrogenation, reduction and decarbonylation positions furfural as a strategic and ultimate industrial source for the production of a wide range of derivatives. Furfuryl amine, furoic acid, alpha-methylfurfuryl alcohol can be produced in one step from furfural. Other important fine chemicals are 2-acetylfuran, 2,5-dimethoxydihydrofuran, 5-dimethylaminomethylfurfuryI alcohol, and others. 

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