Stefano Marcaccini

Synthesis of indole derivatives via isocyanides

Fast and convenient approaches to the indole nucleus from isocyanides are reviewed as a means for the tailored preparation of conveniently functionalized indoles by using the unique reactivity of isocyanides in one-pot multicomponent and cascade reactions.

A Facile Synthesis of β-Lactams Based on the Isocyanide Chemistry

Abstract The reaction between ( E )-cinnamaldehyde ( 1 ), chloroacetic acid ( 2 ), cyclohexyl isocyanide ( 3 ), and amines 4 afforded the expected Ugi 4-CC products 5 , which were easily cyclised to ( E )-1-substituted N -cyclohexyl-2-(1-phenylethen-2-yl)-4-oxoazetidine-2-carboxamides 6 upon treatment with methanolic KOH.

A facile synthesis of 2,5-diketopiperazines based on isocyanide chemistry

Abstract The Ugi four-component condensation (4-CC) between amines 4 , aromatic aldehydes 5 , chloroacetic acid 6 and isocyanides 7 afforded the expected 4-CC adducts 8 which were cyclised to the title compounds 9 upon treatment with ethanolic KOH under ultrasonication.

Isolation of Ugi Four-Component Condensation Primary Adducts: A Straightforward Route to Isocoumarins

Ugi four-component condensation (Ugi-4CC) between 2-formylbenzoic acid, phenacylamine dimethyl acetal, and isocyanides afforded 1H-isochromen-1-ones (isocoumarins). These products, where structure corresponds to the tautomeric enediamine form of the Ugi-4CC primary adducts, were stable enough to allow their isolation and characterization. Stable isocoumarins were also obtained by employing anilines as the amino component in the Ugi four-component condensation.

Sequential five-component synthesis of spiropyrrolidinochromanones.

Herein we report a novel, diastereoselective, one-pot, two-step, sequential synthesis of highly functionalized natural product-like spiropyrrolidinochromanones. The process consists of an Ugi four-component condensation of 3-formylchromones with amines, isocyanides, and glyoxylic acids followed by a nucleophilic conjugate addition and intramolecular cyclization. The experimental simplicity and tolerance to a wide variety of substituents makes this method suitable for combinatorial synthesis.

Synthesis of thiomorpholines by an intramolecular Ugi reaction

The Ugi four-component condensation between 5-oxo-3-thiacarboxylic acids, benzylamines and cyclohexyl isocyanide gave 5-oxothiomorpholine-3-carboxamides. The configuration of bicyclic thiomorpholine derivatives was established by NOESY experiments.

Enols as Feasible Acid Components in the Ugi Condensation

Heterocyclic enols are used for the first time as acid components in an Ugi-type multicomponent condensation. For that purpose, we have chosen enols containing a Michael acceptor, in order to facilitate an irreversible rearrangement of the primary Ugi adduct. The new four-component process leads readily and efficiently to heterocyclic enamines containing at least six elements of diversity.

Studies on alkyl isocyanoacetates and related compounds. Synthesis of 6-arylthio-8-ethoxycarbonyl-4-ethoxycarbonyl-methylaminoimidazo[5,1-b][1,3,5]thiadiazine-2-thiones

N-Ethoxycarbonylmethyl-S-arylthiocarbamoylisothiocyanates upon treatment with NEt 3 and then with HCl afforded 6-arylthio-8-ethoxycarbonyl-4-ethoxycarbonyl-methylaminoimidazo[5,1-b][1,3,5]thiadiazine-2-thiones.

Synthesis of 1-Arylthiocarbonyl-4-isopropylamino-2,5-dihydro-1H-imidazole-2-thiones, a Novel Class of Imidazole Derivatives

The reaction between N-isopropylisocyanoacetamide and arylsulfenyl thiocyanates provides a useful route to 1-arylthiocarbonyl-4-isopropylamino-2,5-dihydro-1H-imidazole-2-thiones, a novel class of imidazole derivatives, whose structure was determined by X-ray analysis

Zinc catalysed ester solvolysis. Application to the synthesis of tartronic acid derivatives

A novel synthesis of hydroxyglycine retropeptidic derivatives was achieved through a Passerini 3-component reaction of glyoxyl amides or esters, followed by an unprecedented environmentally benign zinc catalysed solvolysis.