Application of phosphonyl carbanions to highly regioselective synthesis of some diazaphospholes and pyrazolinyl phosphonates.
A series of substituted spiro[3']pyrazolinylphosphonates and spiro[3]diazaphospholes were synthesized via 1:3-dipolar cycloaddition reaction of 2-diazonio-1,3-dioxo-2,3-dihydro-1H-inden-2-ide with phosphonyl carbanions: diethyl-cyanomethylphosphonate, -phosphono-acetates, and -vinylphosphonate. On the other hand, treatment of the diazo substrate with diethyl (thiomethyl)methylphosphonate led to the formation of condensed oxadiazine and spiro[3]diazaphosphole. Some compounds were found to possess antibacterial and antifungal activities.
Abdou
Wafaa M
WM
Chemical Industries Division, National Research Centre, El-Bohouth St., Dokki, D-12662, Cairo, Egypt. wabdou@intouch.com
Khidre
Maha D
MD
Khidre
Rizk E
RE
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology; D011720:Pyrazoles; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D063065:Organophosphonates; D011720:Pyrazoles