Synthesis, reactions and applications of naphthofurans: A review

Abstract

Considering the highly important biological and medicinal properties of naphthofurans, the synthesis of these heterocycles has attracted the interest of medicinal and organic chemists. This review aims to describe the different strategies developed so far for the synthesis of naphthofurans and their applications and the literature reports for the period of 2000 to early 2020. After a brief introduction of the types of naphthofurans and their biological activities, the different synthetic approaches such as chemical and photochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. Some of the reactions have been applied successfully to the synthesis of biologically important compounds.

Organocatalytic (Z/E)-Selective Synthesis of 3-Vinylnaphthofurans via a Formal (3 + 2) Cycloaddition

“…17 Among them, 1a, 1j-1n, 1p-1r, 1t, 1w, and 1y are known compounds, and the identities of these compounds were confirmed by comparing the measured spectroscopic and physical data with the literature data. 3,136.3 (d,J = 8.0 Hz),136.0,135.9,135.8,133.6,131.29,131.27,128.8,128.6,125.1 (d,J = 12.0 Hz) 9, 191.2, 163.7, 143.1, 139.3, 135.8, 135.7, 133.8, 133.6, 133.2, 130.7, 128.72, 128.69, 127.7, 120.3, 62.5, 14.0 3, 191.9, 163.8, 143.4, 139.6, 137.1, 136.1, 136.0, 133.6, 132.7, 132.1, 130.0, 128.8, 128.7, 125.8, 62.4, 21.1, 14.0 7, 189.9, 164.3, 159.5, 141.5, 138.7, 136.1, 135.2, 133.4, 131.4, 128.70, 128.67, 127.0, 121.1, 111.8, 62.2, 55.9, 14.0;IR (KBr): 1722, 1678, 1597, 1484, 1466, 1353, 1247, 1015 2,187.4,187.3,163.6,162.9 (d,J = 247.0 Hz),145.6,138.3 (d,J = 6.0 Hz),135.8,133.7,132.8,130.7 (d,J = 8.0 Hz),128.8,128.6,124.8,124.7,121.4 1, 187.4, 163.5, 145.7, 137.7, 135.8, 135.4, 134.2, 133.7, 132.8, 130.3, 128.9, 128.8, 128.6, 127.0, 62.6, 13.9;IR (KBr): 1725, 1668, 1597, 1469…”

“…In 2019, Jiang and coworkers 10 employed FeCl 3 as a catalyst and developed an aerobic dehydrogenative cyclization domino reaction of βnaphthyl substituted allenylmethyl ether via a Claisen rearrangement process, leading to the synthesis of disubstituted vinylnaphthofurans (eq 2). In spite of these progresses, great challenges still remain in the construction of vinylnaphthofuran scaffolds, mainly including: (1) constructing multisubstituted vinylnaphthofurans via a cascade reaction; (2) controlling the (Z/E)-selectivity of multisubstituted vinylnaphthofurans; (3) developing organocatalytic reactions for constructing vinylnaphthofurans.…”

“…Moreover, R7000 with a naphthofuran core serves as a candidate antiparasitic drug, and compound I showed significant anticancer activity against human cancer cell lines. As a consequence, great attention has been paid to develop efficient approaches for the construction of naphthofuran scaffolds. − Among them, metal-catalyzed reactions − and organocatalytic reactions are generally the most effective methods toward the synthesis of naphthofurans, which resulted in the rapid development of synthetic methods for naphthofurans.…”

A simple and efficient approach for the synthesis of functionalized naphtho[2,1-b]furan via an one-pot, three-component reaction between Meldrum's acid, arylglyoxals, and β-naphthol

“…Naphthofuran is a bicyclic heterocyclic structure that results from the fusion of a twelve-membered naphthalene ring to a five-membered furan ring. 1 The interest to the synthesis and study of the naphtho [2,1b]furan nucleus is due to the wide spectrum of significant biological activity exhibited by this class of heterocycles, including antibacterial, 2 antimicrobial, 3 anthelmintic, 4 analgestic, 5 and oestrogenic properties. 6 Moreover, naphthofurans and its derivatives are important building units found as key structural motifs in a large number of biologically important natural products (Figure 1).…”

Synthesis, reactions, and applications of chalcones: A review

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Based on the above arguments, in continuation of our program , and related work [62][63][64][65][66][67], therefore, this review aims to highlight and summarize the synthetic methodologies, reactions, applications, and biological activities of chalcones.

Synthetic methodology of chalcones

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