Diastereoselective synthesis of tetraalkyl (R,R)-1,2-cyclohexylene-diamino-di-phosphonates bearing thiophene, furan and pyrrole moieties. Computational and experimental study on their formation

Chrostowska, Anna; Darrigan, Clovis; Khayar, Saïd; Baylère, Patrick; Lewkowski, J.; Krzyczmonik, Anna; Tokarz, Paweł; Ślepokura, Katarzyna; Lis, Tadeusz

doi:10.1016/j.tet.2015.03.010

Cited by 3 publications

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“…The classical method used for the aza-Pudovik reaction, i.e., preparation of a Schiff base from the mixture of an aldehyde with an amine in methanol at room temperature, its isolation and, finally, the reaction of a Schiff base with diphenyl phosphite in boiling acetonitrile or toluene [ 24 , 41 , 42 ], failed to provide the desired pyrrole-derived aminophosphonates. The methodology, which was elaborated during the realization of our previous project [ 43 ], was modified. Pyrrole-derived aminophosphonates were obtained in a two-step reaction, but Schiff bases were not isolated.…”

Section: Resultsmentioning

confidence: 99%

Novel N-Arylaminophosphonates Bearing a Pyrrole Moiety and Their Ecotoxicological Properties

et al. 2017

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A wide range of biological activities of aminophosphonates predisposes them to find applications as anticancer, antiviral, antimicrobial, antifungal, or herbicidal agents. Despite a number of positive aspects of the use of aminophosphonates, their applications may cause a risk to the environment, which is well exemplified by the case of glyphosate. Therefore, scientists see a pressing need to rate ecotoxicity of aminophosphonates. Nowadays, it is recommended to use comprehensive tools to carry out appropriate and effective risk assessments of toxic substances. For these purposes, tests based on the acute toxicity of the luminescent bacteria Aliivibrio fischeri, as well as the measurement of sub-chronic toxicity of the crustacean Heterocypris incongruens seem to be the most convenient. A series of five diphenyl N-arylamino(pyrrole-2-yl)methylphosphonates was synthesized and preliminary evaluation of their ecotoxicological properties was performed. In order to carry out such investigations, we applied the two biotests mentioned above. Results showed that the N-(4-nitrophenyl) derivative was the most toxic for bacteria in comparison to other tested compounds. As for crustaceans, N-phenyl and N-naphthyl derivatives were found to be the most harmful, simultaneously being relatively harmless for bacteria. Such a phenomenon are discussed in correlation with the literature, while its reason is discussed with respect to the aspect of structure of the tested compounds.

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