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We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction ortho-iminophenols and ortho-vinylphenols with MBH carbonates of isatins under mild and metal-free conditions. The selective generation of different kinds of dihydrobenzofuran and benzofuran derivatives was successfully achieved by employing different substituted isatin-derived MBH carbonates with ortho-N-tosyliminophenols and ortho-vinylphenols. The features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, and atomic economy.

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing o-hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(o-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro[cyclobuta[c]chromene-1,3′-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-(o-hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2′,1′:5,6]pyrano[3,4-c]chromene derivatives in high yields and with high diastereoselectivity.

Abstract: A one-pot multi-component reaction is developed for the efficient synthesis of 4,5-dibenzylidene octahydroacridines in high yields. The reaction is performed by the tandem reaction of three molar equivalent aromatic aldehydes with two molar equivalent 4-alkylcyclohexanone in the system of NH4OAc/HOAc under microwave irradiation. MediaObjects/11532_2008_27_Fig1_HTML.jpg

The domino reactions of 1,3-thiazolidinedione, malononitrile, and aromatic aldehydes in the presence of different organic amines were studied. Secondary amines such as pyrrolidine, piperidine, morpholine, and dimethylamine and primary amines such as benzylamine yield dihydrothiophene derivatives through a domino ring-opening/recyclization reaction of 1,3-thiazolidinedione. Bulky diethylamine, diisopropylamine, and 1,4-diazabicyclo[2.2.2]octane give spirocyclohexano-1,3-thiazole through a double Michael addition/spirocyclization reaction.