Convenient synthesis of furan-3-carboxylic acid and derivatives

Zanatta, Nilo; Faoro, Débora; Silva, Simone C.; Bonacorso, Hélio G.; Martins, Marcos A. P.

doi:10.1016/j.tetlet.2004.05.109

Cited by 22 publications

(9 citation statements)

References 14 publications

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“…The synthesis of furan-3-carboxylic acid and derivatives was carried out by Zanatta et al from the aromatization of 4-(trichloroacetyl)-2,3-dihydrofuran with NBS in CCl 4 under reflux conditions (Scheme ). This was followed by nucleophilic displacement of the trichloromethyl group by hydroxide, alcohols, and amines to form the corresponding acid, esters, or amide in high yield.…”

Section: Oxidation Reactionssupporting

confidence: 83%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Oxidation Reactionssupporting

confidence: 83%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…However, only the elimination product was isolated (3‐trichloroacetylfuran 86 ), at 60 % yield (Scheme 25). [111] In order to use the trichloromethyl group as a leaving group under basic conditions, furan 86 was reacted with several alkyl amines (primary and secondary) to furnish furan‐3‐carboxamides 87 , at 68–98 % yields (depending on the nature of the amine). When arylamines were used, the trichloromethyl group was first hydrolyzed to the corresponding furan‐3‐carboxylic acid 88 (refluxing benzene in the presence of NaOH, 70 % yield), then converted to the acyl chloride 89 (SOCl 2 , cat.…”

Section: Synthesis Of Other Heterocyclic Systems With Promising Biological Activitymentioning

confidence: 99%

Haloacetylated Enol Ethers: a Way Out for the Regioselective Synthesis of Biologically Active Heterocycles

2021

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This review describes advances in the synthesis of heterocyclic scaffolds (associated with their biological activity), using haloacetylated enol ethers as precursors. The wide variety of heterocycles that can be prepared using these precursors, together with the high regioselectivity they usually provide, in [3+2] and [3+3] cyclocondensation reactions, make these starting materials powerful tools. The biological evaluation is also highlighted, given that several analogues of commercially available drugs can be easily accessed.

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“…However, the introduction of a substituent to the 3-position of furans requires special strategies. Several such procedures have been developed, one of which is the synthesis of furan-3-carboxylic acid (63) via aromatization of 3-trichloroacetyl-4,5-dihydrofuran (62) followed by a nucleophilic displacement with hydroxide, alcohols and amines (Scheme 6.25) [66]. (65) in high yields (Scheme 6.26).…”

Section: Monosubstituted Furansmentioning

confidence: 99%