Abstract
Dihydronaphthofurans (DHNs) are an important class of arene ring-fused furans which are widely found in many natural and non-natural products and drug candidates with relevant biological and pharmacological activities. Furthermore, vinylidene-naphthofurans exhibit photochromic properties when exposed to UV or sun light at room temperature. For these reasons, a vast array of synthetic procedures for the preparation of dihydronaphthofurans including annulation of naphthols with various reagents, cycloaddition reactions ([3 + 2], [4 + 1] and Diels–Alder), intramolecular transannulation, Friedel–Crafts, Wittig, Claisen rearrangement, neophyl rearrangement and other reactions under various conditions have been developed over the past decades. This review aims to describe the different strategies developed so far for the synthesis of dihydronaphthofurans and their applications. After a brief introduction to the types of dihydronaphthofurans and their biological activities, the different synthetic approaches such as chemical, photochemical, and electrochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. The subsequent section focuses on biological and pharmacological applications and photochromic properties of the target compounds.
Highlights
Furans are ve-membered aromatic heterocycles containing one oxygen atom that are commonly found in many importantAssociate Professor Dr Abolfazl Olyaei was born in Tabriz, Iran in 1975
Associate Professor Dr Mahdieh Sadeghpour was born in Qazvin, Iran, in 1978
Several reports on the synthesis of hemiacetals of dihydronaphthofurans have been described by Dibble et al 1,3Dihydro-1-hydroxynapbtho[2,3-c]furan (43) and 1,3-dihydro-lhydroxynaphtho[1,2-c]furan (44) could be successfully prepared in 77% and 85% yields, respectively
Summary
Associate Professor Dr Abolfazl Olyaei was born in Tabriz, Iran in 1975. He received his B.Sc. degree in pure chemistry from the University of Tabriz in 1999. Some of the synthesized dihydronaphthofuran derivatives exhibit a variety of interesting biological and pharmacological properties including 5-lipoxygenase inhibitor,[7] C17,20 lyase inhibitors,[8] antitubercular activity against Mycobacterium tuberculosis H37Rv,[9] anti-tyrosinase, antioxidant, and antibacterial,[10] inhibitors of NF-kB activity,[11] a-glucosidase inhibitors,[12] inhibitor of a-chymotrypsin[13] and anti cancer activities (liver tumor growth inhibitors).[14] vinylidene-naphthofurans are a new class of polycyclic compounds that exhibit photochromic properties when exposed to the UV or sunlight at room temperature and adsorbed in silica gel or dissolved in acidi ed alcoholic solutions (Fig. 2).[15,16,17,18,19,20]. Review neophyl rearrangement and the other reactions in various conditions and their biological, pharmacological and photochromic properties
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