Five-membered ring systems: furans and benzofurans

Kwiecień, H.

doi:10.1016/b978-0-323-98410-2.00007-2

Cited by 5 publications

(1 citation statement)

References 167 publications

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“…[7] Hence, many researchers have focused on a large number of b-fused furans compare to c-fused furans. [8][9][10][11] There are ample of review available in the literature on benzo-bfuran [7,[12][13][14][15][16][17][18] than IBF/benzo-c-furan, [17][18][19][20][21][22] while the number of review on 3,4-fused furan/c-fused furan is strikingly less. [14,15,23] Benzo c-furan (iso benzofuran) 3 is a class of c-fused furan.…”

Section: Introductionmentioning

confidence: 99%

A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

Manna¹,

Giri

Mondal³

et al. 2023

ChemistrySelect

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c‐fused furan and their derivatives are widely used as essential components of agrochemicals, bioregulators, dyes, essential skin and hair oils, cosmetics, flavouring agents, photosensitizers in industry and also show a broad range of biological activity. To the best of our knowledge, as of yet, no review has been published that covers the entire synthetic pathway leading to the formation of just c‐fused or 3, 4‐fused furans. In this review, we outline the various pathways for bicyclic, tricyclic, and polycyclic c‐fused furans, along with their detailed mechanisms, concrete examples, and biological activity. We have focused particularly on the synthetic route to medicine, natural products, and their analogues, such as c‐fused furanoditerpenes isospongiadiol, radermachol, a potential folk medicine ingredient, furo[3,4]quinolin‐4(5H)‐ones core, an inhibitor of lymphoma, bhimamycin B, hibiscone‐c core moiety of antibiotic lactonamycin, and analogue of natural product furanether A/ furanether B. Previous approaches and recent methods are described including metal‐free, transition metal, bio‐catalyst, and multi‐substrate approaches with mechanisms. The review covers the literature for more than six decades and presents an overview of the synthesis of different c‐fused furans and their utility in various disciplines such as synthetic chemistry, medicinal chemistry, and drug discovery.

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Section: Introductionmentioning

confidence: 99%

A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

Manna¹,

Giri

Mondal³

et al. 2023

ChemistrySelect

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Palladium‐Catalyzed Cyclizative Borylation of Allenyl Ketones through Carbene Boryl Migratory Insertion: Access to Densely Substituted Furyl Boronates

Wang

2023

Chemistry A European J

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Herein the palladium-catalyzed cyclizative borylation of allenyl ketones with diboron compounds is reported which involves the carbene boryl migratory insertion as the key step. This reaction features mild conditions, good functional group tolerance and broad substrate scope. Thus, it represents an efficient methodology for the assembly of diverse tri-substituted furyl boronates. In addition, a series of transformations of the resultant multi-substituted furyl boronates were conducted to provide various densely substituted furan derivatives in good yields, further illustrating the potential synthetic utility of this methodology.

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Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N‐Acetylglucosamine into Unsubstituted 3‐Acetamidofuran by Retro‐Aldol Condensation

et al. 2023

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Aminofurans are widely used in drug synthesis as aromatic modules analogous to aniline. However, unsubstituted aminofuran compounds are difficult to prepare. In this study, a process for the selective conversion of N‐acetyl‐d‐glucosamine (NAG) into unsubstituted 3‐acetamidofuran (3AF) is developed. The yield of 3AF from NAG catalyzed by a ternary Ba(OH)2−H3BO3−NaCl catalytic system in N‐methylpyrrolidone at 180 °C for 20 min can reach 73.9 %. Mechanistic studies reveal that the pathway to 3AF starts with a base‐promoted retro‐aldol condensation of the ring‐opened NAG, affording the key intermediate N‐acetylerythrosamine. Judicious selection of the catalyst system and conditions enables the selective conversion of biomass‐derived NAG into 3AF or 3‐acetamido‐5‐acetylfuran.

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Five-membered ring systems: furans and benzofurans

Cited by 5 publications

References 167 publications

A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

Palladium‐Catalyzed Cyclizative Borylation of Allenyl Ketones through Carbene Boryl Migratory Insertion: Access to Densely Substituted Furyl Boronates

Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N‐Acetylglucosamine into Unsubstituted 3‐Acetamidofuran by Retro‐Aldol Condensation

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