Synthesis and antimicrobial activity of novel 2-alkyl/arylcarbamato-6-(1,1-dimethylethyl)-3-cyclohexyl-3,4-dihydro-2H-1,3,2-benzoxazaphosphorine-2-oxides

• Published in: Journal of heterocyclic chemistry Vol. 39; no. 5; pp. 1039 - 1044
• Main Authors: Babu, Y. Hari, Reddy, P. Vasu Govardhana, Reddy, C. Suresh, Reddy, C. Devendranath, Devi, P. Uma Maheswari
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley-Blackwell 01-09-2002; Wiley‐Blackwell
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570390529

Novel 2‐alkyl/arylcarbamato‐6‐(1,1‐dimethylethyl)‐3‐cyclohexyl‐3,4‐dihydro‐2H‐1,3,2‐benzoxaza‐phosphorine‐2‐oxides (IV) have been synthesized from reactions of 2‐cyclohexylaminomethyl‐4‐t‐butylphenol I [8c] with various dichlorophosphinyl carbamates (III) [8a‐b] in dry toluene in the presence of triethylamine at 40‐50 °C. All the title compounds (IVa‐j) at reflux temperature are degraded to 2‐amino‐6‐(1,1‐dimethylethyl)‐3‐cyclohexyl‐3,4‐dihydro‐2H‐1,3,2‐benzoxazaphosphorine‐2‐oxide (IVk) exclusively. The structures are determined by ir, nmr and mass spectral studies. They were screened for antifungal activity against Penicillium notatum, Aspergillus niger and Helminthosporium sps, and antibacterial activity on Escherchia coli, Staphylococcus aureus and Pseudomonas aeruginosa. A few of them possess significant activity.