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

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).

Key Words:

• Selenium compounds
• diaryl selenides
• diaryl selenones
• Schiff bases