ORGANIC SELENIUM COMPOUNDS. PART I: SYNTHESIS AND APPLICATION OF SOME NEW DIARYL-SELENIDES AND SELENONES CONTAINING AMINO ACID MOIETIES

Abstract

Abstract 4′-Nitro-4-aminodiphenylselenide (1) reacts with chloroacetyl chloride giving 4′-nitro-4-chloroacetylaminodiphenylselenide (2) which undergo facile reaction with certain amines and hydrazine yielding 4′-glycylamino and hydrazinoacetylamino-4′-nitrodiphenylse lenides (3) and (5). Two moles of (2) react with one mole of piperazine and/or hydrazine to give 1,4-bis [p-N-(p′-nitro-diphenylselenido)aminocarbonylmethylene] piperazine (4) and 1,2-bis[p-N-(p′-nitro-diphenylselenido)aminocarbonyl-methylene]hydrazine (6). Condensation of (5) with aromatic aldehydes in the presence of glacial acetic acid yielded new Schiff bases (7). N-phthaloylglycyl chloride reacts with (1) in dioxane in the presence of trimethylamine to give N-(N′-phthaloylaminoacyl)-4-aminodiphenylselenide (8), hydrazinolyses of which affords N-(aminoacyl)-4-amino-4′-nitrodiphenylselenide (9). Compound (9) undergoes facile condensation with aromatic aldehydes in the presence of piperidine to give Schiff bases (10). Compound (2) interacts with malononitrile in the presence of K2CO3, giving 2-amino-(p′-nitrodiphenylselenido)-5-oxo-Δ2-pyrrolin-3-carbonitrile (11). Oxidation of (3,7) and (10) using H2O2/gl. acetic acid mixtures furnished the corresponding diarylselenones (12,13 and 14).