Efficient Synthesis and Antimicrobial Evaluation of New Organophosphorus Dioxaspirodecanone Derivatives | ||||
| Egyptian Journal of Chemistry | ||||
| Article 48, Volume 65, Issue 12, December 2022, Page 533-542 PDF (956.42 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2022.140804.6159 | ||||
 View on SCiNiTO | ||||
| Authors | ||||
Hala Ramadan El-Shanawany1; Soher Said Maigali2; Naglaa Fathy El-Sayed   3; mohamed adel youssef4; Mohamed ELsayed Abdel-Aziz 5
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| 1Organometallic and Organometalloid Chemistry Department, Chemical Industries Institution, National Research Centre | ||||
| 2Organometallic and Organometalloid Chemistry Department, Chemical Industries Institute, National Research CentreNational Research Centre, 30 El-Tahrir Street | ||||
| 3Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, P.O. 12622, Giza, Egypt. | ||||
| 4Chemistry department, Faculty of science, Helwan University, Cairo, Egypt. | ||||
| 5Microbial Chemistry Department, Genatic Engineering and Biotechnology Institute, National Research Centre, 33 ElBohouth St., (Former El Tahrir), | ||||
| Abstract | ||||
| Claisen-Schmidt condensation reaction of 1,4-cyclohexanedione monoethyleneketal (1) with p-methoxybenzaldehyde, under base catalyzed conditions, has afforded 7,9 bis (4-methoxybenzylidene)-1,4-dioxaspiro[4,5]decan-8-one (2). The bis-benzylidene 2 was functionalized with some selected organophosphorus reagents. Thus, compound 2 was reacted with tris-(dialkylamino) phosphines 3a,b, in refluxing toluene and in presence of a catalyst, to give a products mixture of the corresponding oxaphospholedioxolane oxides 8a,b and tetraalkylphosphonicdiamides 9a,b. Moreover, the reaction of bis-benzylidene 2 with the trialkylphosphite reagents 4a,b afforded the corresponding alkyl- phosphonate derivatives 10a,b. The phosphonate 10b could be also obtained upon reacting bis-bezylidene 2 with diisopropylphosphite (5) under the same experimental conditions. The reaction of bis-benzylidene 2 with the stable phosphoniumylides, namely, (carbmethoxymethylene)-, or (carbethoxymethylene) -triphenylphosphorane (6a,b) , afforded the dihydrospiroindenedioxolanone derivative 11 under the given reaction conditions. Moreover, compound 11 was also obtained from reactions of the dialklyphosphonoacetate Wittig-Horner reagents 7a,b with compound 2. On the other hand, reaction of diethyl(cyanomethylene) phosphonate 7c with bis-bezylidene 2, in an ethanolic sodium ethoxide solution, gave the 1,4- dispiroylidene acetonitrile derivative 12. Possible reaction mechanisms are discussed and the structures of the new products are confirmed from their analytical and spectroscopic data. The antimicrobial activity of the synthesized compounds was also investigated. | ||||
| Keywords | ||||
| Bis- benzylidene; Organophosphorus reagents; Antimicrobial agents | ||||
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