Synthesis of furan substituted dihydrofuran compounds by radical cyclization reactions mediated by manganese(III) acetate

Abstract

In this study, novel furan substituted dihydrofuran compounds were synthesized by the radical addition of 1,3-dicarbonyl compounds to 1,1-and 1,2-disubstituted alkenes using manganese(III) acetate in HOAc. It is observed that 1,1-disubstituted alkenes gave better yields whereas 1,2-disubstituted alkenes gave moderate yields. Besides, 1,2-disubstituted alkenes gave us cisisomers whereas trifluoromethylated 1,3-dicarbonyl compounds with 1,2-disubstituted alkenes gave us trans-isomers of dihydrofuran determined by NOSY spectra.

Acetylcholinesterase inhibition, molecular docking and ADME prediction studies of new dihydrofuran-piperazine hybrid compounds

“…AChE (from electric eel, type V-S), acetylthiocholine iodide (ATCI), 5,5′-dithiobis(2nitrobenzoic acid) (DTNB) were supplied from Sigma Aldrich. Radical oxidant Mn(OAc)3 was synthesized by electrochemical method [43].…”

“…Manganese(III) acetate [33][34][35][36][37] and Cerium(IV) ammonium nitrate [38][39][40] are the most widely used transition metal salts in this reaction. Our research group has reported the synthesis of dihydrofuran compounds by the radical cyclization of 1,3-dicarbonyl compounds with various unsaturated systems such as aromatic conjugated alkenes [41,42], dienes [43,44] and conjugated amide derivatives [45,46] mediated by Manganese(III) acetate and Cerium(IV) ammonium nitrate.…”

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

“…further explored the manganese(III) acetate mediated radical addition reaction of trifluoromethyl‐β‐dicarbonyl compounds 1 with various substituted alkenes 32 , 34 and 36 , leading to the formation of dihydrofuran derivatives of type 33 , 35 and 37 , respectively (Scheme 10). [82–84] Notably, trans ‐isomers 37 were obtained in the reaction of trifluoromethyl‐β‐dicarbonyl compounds 1 with various 1,2‐disubstituted alkenes 36 . Reaction of 1 with 2‐thienyl and 2‐furyl substituted alkenes 28 led to the synthesis of dihydrofurans containing trifluoromethyl ketone 29 and trifluoromethyl group 31 [85] .…”

Recent Advances in Manganese(III)-Assisted Radical Cyclization for the Synthesis of Natural Products: A Comprehensive Review

“…Similarly, aldehydes, ketones, monocarboxylic acids and their anhydrides, β-dicarbonyl compounds (such as β-diketones), β-keto esters, β-keto carboxylic acids and amides, malonic acid and its derivatives, and β-nitro carbonyl compounds are oxidized by manganese(III) acetate to attain a variety of products [15]. Manganese(III) mediation in reactions not only provides oxidative cyclization [16][17][18][19][20][21][22][23][24][25][26][27][28][29], but also enables highly diversified acetoxidation [30][31][32][33][34], halogenation [35,36], aromatization [37][38][39], oxidation [40,41], phosphonation [42,43], epoxidation [44], and also polymerization [45]. Cyclization occurs via two different mechanisms: intermolecular and intramolecular.…”