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An interesting and simple method was developed for the synthesis of 2-(alkylamino)-3-cyanobenzofurans by consecutive C–C, C–O, and C–N coupling reaction of methyl (–)-3-dehydroshikimate with malononitrile and a bromoalkane or dibromoalkane under microwave conditions. This process represents a metal-free sustainable strategy for the construction of 2-(alkylamino)-3-cyanobenzofurans from a biomass-derived starting material.

An efficient method for the assembly of novel and diversified benzo-fused N-heterocycles mediated by the biomass-derived N-arylated 2-aminophenol (1) has been established. Four kinds of benzo-fused N-heterocycles with six- to eight-membered ring systems, including N-arylated dibenzo[b,e][1,4]oxazepin-11(5H)-ones (4), acridones (5), 7,12-dihydrodibenzo[b,e][1,4]oxazocin-6H-ones (6) and dibenzo[b,f]azepin-10(11H)-ones (7) have been efficiently synthesized in good to excellent yields, respectively. This process is comprised of the N-arylation reaction between N-arylated 2-aminophenols (1) and 2-halogenated benzoic or phenylacetic acids to afford a series of mutli-functionalized triarylamines (3), followed by chemo- and regio-selective intramolecular lactonization or acylation under mild conditions.

A biomass-based, metal- and ligand-free assembly of N-aryl-1,4-benzoxazin-3-ones from methyl 3-dehydroshikimate (3-MHDS), involving aliphatic to aromatic transformation followed by C–O and C–N forming reactions, is presented. A variety of N-aryl-1,4-benzoxazin-3-ones were efficiently synthesized in a one-pot consecutive manner under microwave conditions.

A facile and one-pot method for the synthesis of N-aryl-2(3H)-benzoxazolones via microwave-assisted consecutive reactions between the biomass-derived methyl 3-dehydroshikimiate (3-MDHS), anilines and bis(trichloromethyl) carbonate (BTC) is reported. The protocol includes the efficient generation of the platform compounds N-arylated 2-aminophenols, followed by the smooth annulation reaction induced by BTC. This sequential process represents a metal-free, sustainable and functional group compatible method for the rapid construction of N-aryl-2(3H)-benzoxazolones.

An interesting and simple method was developed for the synthesis of 2-(alkylamino)-3-cyanobenzofurans by consecutive C–C, C–O, and C–N coupling reaction of methyl (–)-3-dehydroshikimate with malononitrile and a bromoalkane or dibromoalkane under microwave conditions. This process represents a metal-free sustainable strategy for the construction of 2-(alkylamino)-3-cyanobenzofurans from a biomass-derived starting material.

This facile and metal-free protocol affords benzoxazinone derivatives in a one-pot manner through sequential reaction between dehydroshikimate, anilines, and bifunctional chloroalkyl esters.