Furans Reactions and Synthesis

Furans are volatile, fairly stable compounds with pleasant odours. Furan itself is slightly soluble in water. It is readily available, and its commercial importance is mainly due to its role as the precursor of the very widely used solvent tetrahydrofuran (THF). Furan is produced by the gas-phase decarbonylation of furfural (2-formylfuran, furan-2-carboxaldehyde), which in turn is prepared in very large quantities by the action of acids on vegetable residues mainly from the manufacture of porridge oats and cornflakes. Furfural was first prepared in this way as far back as 1831 and its name is derived from furfur which is the latin word for bran in due course, in 1870, the word furan was coined from the same root. 

The aromatic furan ring system, though not found in animal metabolism, occurs widely in secondary plant metabolites, especially in terpenoids perillene is a simple example. Vitamin C, ascorbic acid, is at the oxidation level of a trihydroxyfuran, though it assumes an unsaturated lactone tautomeric form. Though one normally associates thiols with unpleasant odours, furfuryl thiol is present in the aroma of roasted coffee. Some 5-nitrofurfural derivatives are important in medicine, Nitrofurazone, a bactericide, is a simple example. Ranitidine is one of the most commercially successful medicines ever developed it is used for the treatment of stomach ulcers. 

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