Preparation of 2,3-Dihydrofurans via a Double Allylic Substitution Reaction of Allylic Nitro Compounds

Abstract

A one-step conversion of allylic nitro compounds to substituted 2,3-dihydrofurans has been developed. Allylic nitro compounds, which are readily available from nitroalkenes and formaldehyde, underwent a double allylic substitution reaction catalyzed by a palladium complex to give 2,3-dihydrofurans in good yield.

Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

“…Following the procedure (b) using 1 (218 mg, 2 mmol), 2c (102 mg, 1 mmol), and Et 3 N (101 mg, 1 mmol) a mixture of products 3c, 4c and 5c was obtained. Subsequent purification gave 3c (120 mg, 40%), 4c (29, mg 15%) and 5c (16 mg, 75% pure as determined by 1 (11), 164 (20), 151 (22), 136 (26), 123 (65), 108 (14), 107 (15), 106 (16), 93 (26), 69 (16), 65 (11), 59 (21), 58 (25), 57 (11), 43 (100), 42 (13) (12), 123 (25), 93 (15), 59 (17), 58 (19), 43 (100), 42 (12), 41 (43), 39 (26).…”

“…[12][13][14][15][16] Synthetic approaches to 2,3-dihydrofurans involve the [4+1] cycloaddition of enones with diazo compounds, 17,18 the [3+2] cyclization of aldehydes with β-ketosulfides/βketosulfones. 11,[19][20][21] For this purpose, the ring closing reaction of 1,3-dicarbonyl compounds with alkenes is efficient as well. [22][23][24][25] Cyclization of the but-3-yn-1-ols is also a method of choice for the synthesis of 2,3dihydrofurans.…”

Ruthenium-catalyzed divergent deaminative and denitrative C–N cleavages: facile access to quinoxalines

“…More significantly, compared to deaminative disconnection via the C–N bond amine cleavage, the denitrative cleavage of C–NO 2 has been rarely accomplished. 15 To date, Ru-catalyzed denitrative transformations have not been realized, and especially the catalytic denitrative annulation using nitroalkanes as an electrophilic C synthon has been entirely unprecedented.…”

Radical Based Strategy toward the Synthesis of 2,3-Dihydrofurans from Aryl Ketones and Aromatic Olefins

“…These scaffolds are used in 1,3-dipolar cycloaddition reactions to synthesize heterocyclic compounds with different ring size and atoms . Given the importance of 2,3-dihydrofurans in natural and synthetic substances, the development of a selective and straightforward intermolecular approach to construct polysubstituted dihydrofurans from simple and economical chemical reagents is still in great demand. − …”