Add time:08/27/2019         Source:sciencedirect.com

Publisher SummaryThis chapter is principally concerned with the preparation and reactions of the furan primary amines 1 and 2. Related secondary and tertiary amines, and also amides and similar N-substituted amines have been included where necessary. The structures of four 2-aminofuran derivatives and 3-aminofuran have been determined by X-ray crystallography. The physical properties of both 2-aminofurans and 3-aminofurans are studied where molecular structure, computational studies, ultraviolet spectroscopy, and NMR spectroscopy are described. The preparation of 2-aminofurans is discussed through various methods— namely, cyclisation of nitriles (from g-keto-nitriles, from g-hydroxy-nitriles, from a,b-unsaturated ketones and cyanide, and other methods employing nitrile cyclisation); reduction of 2-nitro and 2-azido derivatives; rearrangement of furan-2-carboxylate derivatives; substitution of the furan ring; oxazole cycloaddition; elimination from dihydrofuran derivatives; and also miscellaneous methods. And the preparation of 3-aminofurans is discussed through the cyclisation of cyanovinyl ethers; rearrangement of furan-3-carboxylate derivatives; substitution of the furan ring; and miscellaneous methods. The chapter has also described various reactions of both 2-aminofurans and 3-aminofurans. For 2-aminofurans reactions, the reactions of the furan ring (oxidation, reaction with oxygen nucleophiles, reaction with nitrogen nucleophiles, reaction with electrophiles, and cycloaddition reactions) and reactions of ring substituents (reactions of 2-amino substituents, reactions of other substituents, formation of furo[2,3-b]pyridines and furo[2,3-d]pyrimidines, and formation of furo[3,2-b]thiazines and furo[2,3-d]thiazoles) are described. And for 3-aminofurans reactions, the reactions of the Furan Ring (Oxidation, Reaction with Nucleophiles, Reaction with Electrophiles, and Cycloaddition Reactions) and reactions of Ring Substituents (Reactions of 3-Amino Substituents and Reactions of Other Substituents) are described.

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