Synthesis and Bioactivity of Some New 3-Alkyl-2, 4-diisopropyl-1, 2, 4, 5-tetrahydro-benzo[e][1, 3, 2]-diazaphosphepine 3-sulfides/selenides. Issue 3 (2008)

• Record Type: Journal Article
• Authors: Mohan, Ch.; Raju, C. Naga; Rao, A. Janardhan
• Is Part Of: E-Journal of Chemistry. Volume 5:Issue 3(2008)
• Page Start: 479
• Page End: 486
• Publication Date: 2008
• Subjects: α, α′-Dibromo-o-xylene, Isopropylamine, Phosphorus tribromide, Grignard reagents, Sulfur, Selenium, Antibacterial activity.
• DOI: 10.1155/2008/594036
• Languages: English
• ISSNs: 0973-4945

Abstract

Abstract : Preparation of a series of novel seven membered heterocyclic compounds, 3-alkyl-2, 4-diisopropyl-1, 2, 4, 5-tetrahydro-benzo[e][1, 3, 2] diazaphosphepine 3-sulfides / selenides (8a-l ) was accomplished in four steps. The synthetic route involves α, α ′ -dibromo- o -xylene (1 ) with two moles of isopropylamine (2 ) in the presence of triethylamine (TEA) in dry tetrahydrofuran (THF) at low temperature to form the compound 3 . This on treatment with phosphorus tribromide (4 ) in the presence of TEA in dry THF to form the corresponding phosphorobromodite (5 ). This on subsequent reaction with different Grignard reagents (6 ) in dry THF under N2 atmosphere formed the compounds 7 . They are converted to the corresponding sulfides and selenides (8a-l ) by reacting them with sulfur and selenium respectively. Their structures were established by elemental analysis, IR, 1 H, 13 C, 31 P NMR and mass spectral data. All the title compounds were screened for their antibacterial activity. Most of the compounds exhibited significant antimicrobial activity.