Use of Microwave Heating in the Synthesis of Heterocycles from Carbohydrates
Maria Assunta Chiacchio,
This review concerns the role of microwave irradiation in the synthesis of heterocycles starting from carbohydrates. This topic
has received increasing interest owing to the wide variety of heterocyclic compounds as biologically significant chiral natural products or
drugs, and products for industrial application, which cover nearly all aspects of carbohydrate chemistry. In particular, the possibility of
employing microwave irradiation as a source of energy together with simple low-molecular-weight carbohydrates, as attractive chiral raw
materials, has led to the production of low-cost and eco-friendly heterocycles within the framework of a green chemistry approach.
Moreover, the employment of small amounts of solvents or solvent-free systems with solid supports, enables reaction completion in
much shorter times under more environmentally clean conditions and preparation of the target compounds on the scale of grams, without
the risk of any major hazards. The many possible combinations of skeletal, building block, and stereochemical diversity elements make
this a highly attractive synthetic approach.
This review covers the period from the first utilization of microwave irradiation until 2012 and includes the syntheses of (i) heterocycles
linked directly or via a tether to carbohydrates, (ii) heterocycles annulated with carbohydrates, (iii) heterocycles from carbohydrates via
hetero-Diels-Alder (HDAR) and Diels-Alder (DAR) reactions, or via 1,3-dipolar cycloadditions, with particular regard to the “click reaction”
(CuAAC), (iv) iminosugars, and (v) 5-hydroxymethylfurfural.
Keywords: Carbohydrates, click reactions, cycloaddition reactions, green chemistry, heterocycles, iminosugars, microwave.
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