Organic selenium compounds. Part I: Synthesis and application of some new diaryl-selenides and selenones containing amino acid moieties

Article abstract of DOI:10.1080/10426500008043676

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′-nitrodiphenylselenides (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 triethylamine 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-Δ ²-pyrrolin-3-carbonitrile (11). Oxidation of (3,7) and (10) using H₂O₂/gl. acetic acid mixtures furnished the corresponding diarylselenones (12, 13 and 14).

Full text of DOI:10.1080/10426500008043676

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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ORGANIC SELENIUM
COMPOUNDS. PART I:
SYNTHESIS AND APPLICATION
OF SOME NEW DIARYL-
SELENIDES AND SELENONES
CONTAINING AMINO ACID
MOIETIES
M.A. Abbady a & Sh. H. Abdel-Hafez a
a Chemistry Department, Faculty of Science, Assiut
University, Assiut, Egypt
Version of record first published: 04 Oct 2006.
To cite this article: M.A. Abbady & Sh. H. Abdel-Hafez (2000): ORGANIC SELENIUM
COMPOUNDS. PART I: SYNTHESIS AND APPLICATION OF SOME NEW DIARYL-SELENIDES
AND SELENONES CONTAINING AMINO ACID MOIETIES, Phosphorus, Sulfur, and Silicon
and the Related Elements, 160:1, 121-139
To link to this article: http://dx.doi.org/10.1080/10426500008043676
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