Enzo Castagnino

Decarboxylative radical addition onto protonated heteroaromatic systems including purine bases

Abstract Irradiation of esters 2 derived from carboxylic acids and N -hydroxypyridine-2-thione 1 in the presence of anhydrous camphorsulphonic acid and various heteroaromatic systems including purines affords the corresponding adducts in moderate to good yield.

The preparation of a novel 3-oxo-cyclopenten-2-phosphonate derivative, useful intermediate for 2-alkyl-substituted cyclopentenones synthesis.

Abstract Starting from a phosphonyl-furylcarbinol derivative, diethyl(l-methyl-3-oxo-cyclopenten-2-yl)phosphonate, first example of oxocyclopentenyl-phosphonate and useful intermediate for the synthesis of 2-alkylsubstituted cyclopentenones, has been prepared.

The use of acyl derivatives of N-hydroxy-2-thiopyridone in a simple synthesis of pyrrolidines and tetrahydrofurans

Photolysis of the N-hydroxy-2-thiopyridone derivatives of 3-N-acetylallylamino, 3-N,N-diallylamino and 3-allyloxy-propionic acids gave cleanly derivatives of N-acetyl-3-methylpyrrolidine, N-allyl-3-methylpirrolidine and of 3-methyltetrahydrofuran respectively. The corresponding reaction with 3-allylthiopropionic acid afforded a radical which fragmented to ethylene and the allylthio radical without cyclization.

An effective method for the synthesis of unsymmetrical difurylmethane derivatives and 1,1-difuryl olefins

Abstract Unsymmetrical difurylmethane derivatives 9 and the unknown difuryl alkenes 10 were selectively obtained from carbinols 1a and 1b in two steps and with excellent yields.

Studies on Reactivity of Furyl-Phosphonyl-Carbinols. An Effective One-Step Synthesis of 2-Methylphosphonyl-5-Alkoxymethyl-Furans

Abstract A simple ‘one pot’preparation of the novel 2,5-disubstituted furans 3a-e directly from carbinol 1, is described.

Photochemical Cleavage of Supercoiled DNA by N-Acyloxypyridine-2-thione Acridinyl Derivatives

New acyl thiohydroxamates bearing an acridine moiety able to intercalate DNA double strand exhibit the capacity to cleave supercoiled DNA to linear DNA. EPR spin-trapping analysis has been employed to detect the formation of the carbon-centered radicals.

Studies on the reactivity of 2-furylhydroxymethylphosphonates: synthesis of 1-oxo-4-hydroxycyclopent-2-en-5-ylphosphonates

Starting from 2-furylhydroxymethylphosphonates (1), a facile and direct preparation of the previously unknown phosphonate-containing cyclopentenones (5), potential new synthons in the elaboration of rethrolone- and prostaglandin-related compounds, is described.