Roberto Pepino

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.

Synthesis and fluorescence of some thiazole and benzothiazole derivatives

Abstract The optical properties of a series of thiazole and benzothiazole styryl derivatives are reported. The effect of lengthening the conjugative system in several thiazolyl- and benzothiazolyl-vinyl stilbenes which were prepared and tested as fluorescent whitening agents is discussed.

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.

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

STUDIES ON ISOCYANIDES. SYNTHESIS OF N-TOSYLGUANIDINES

Abstract The reaction between isocyanides 1 , anilines 2 , and chloramine T ( 3 ) affords N -sulfonylguanidines 4 . The reaction mechanism is discussed in the light of experimental evidences that confirm the initial formation of N -chloroanilines.

A facile synthesis of 1-aryl-2-artylthio-1H-imidazoles

The reaction between the hitherto unknown 2,2-diethoxy-1-isocyanoethane with sulfenyl chlorides and arylamines afforded isothioureas which were cyclized to give the title compounds

A novel class of nitrile ylide

Abstract Isothiocarbamoyl chlorides IV on treatment with NEt 3 afforded nitrile ylides V which reacted with dimethyl acetylenedicarboxylate to give 2 H -pyrroles VI and with ethyl cyanoformate to give 4 H -imidazoles VII.

Permanganate oxidation of 3-methyl-4-nitro-5-styrilisoxazole: a correction

Abstract In contrast with a previous report, permanganate oxidation of the title compound 3 gives the nitroisoxazolone 8 and not 3-methyl-4- nitroisoxazole-5-carboxylic acid 2 ; a reaction pathway, involving the spirocyclisation of the carboxylate 10 , is suggested.