Synthesis and Thermal Isomerization of Carboxylic and Phosphonic α-Aminoesters Substituted With a Triazole Ring

Chemistry of Phosphorylated Formaldehyde Derivatives. Part I

“…The reaction of compounds 282 with sodium azide leads to diethyl [( N -acylamino)azidomethyl]-phosphonates 314 , valuable precursors in the synthesis of phosphinoyl-substituted 1,2,3-triazoles, the products of 1,3-dipolar addition to disubstituted alkynes [173,174]. A mixture of the resultant two regioisomers of diethyl [( N -acylamino)(1-(1,2,3-triazolyl))methyl]phosphonates ( 315 ) and diethyl [( N -acylamino)(2-(1,2,3-triazolyl))methyl]phosphonates ( 316 ) can be separated by chromatography on silica gel (Scheme 107).…”

“…Prolonged heating of acetonitrile solutions of 315 leads to migration of [( N -acylamino)(diethylphosphinoyl)]methyl group from the first to the second nitrogen atom (N1–N2 migration) of 1,2,3-triazole group to give 316 . In the presence of nucleophiles, azide ion or imidazole, the triazole fragment is displaced to yield diethyl [( N -acylamino)azidomethyl]phosphonates 314 or diethyl [( N -acylamino)(1-imidazolyl)methyl]phosphonates 317 (Scheme 108) [174].…”

The intelligence way of economical synthesis strategies of an N-alkylcarbazole

“…The carbazole nucleus can be naturally found in the composition of some alkaloids as staurosporine, ellipticine or koenidine, with antibacterial, antifungal, antimalarial properties, antitumoral activity, and potential antidiabetic effect [6,7,8], among them carbazomycins represent an unprecedented class of antibiotics with a carbazole heterocycle [9]. Various researches done on the synthesis of new heterocyclic compounds [10,11,[12][13][14][15][16][17][18], we focused in this work, on the theoretical study of the reaction carried out followed by the effective synthesis of the 9-(prop-2-yn-1-yl)-9H-carbazole with three methods (phase transfer catalysis, microwave, and base + acetone) with the aim to elaborate a new active molecules with an important yield. For us, it is preferable to establish a theoretical study of a synthetic reaction before going to the experimental mode because it will inform us from the start on the path of the reaction and the expected results to save time and minimize losses of energy (use of heating or not) and matter (reaction possible or not).…”

Naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate

“…It has been the subject of several publications in order to improve regioselectivity, reduce reaction times, and use much greener catalysts, which often contain metals [17,18]. Thus remarkable work has been done by previous researchers in our laboratory for the synthesis of triazolic α-amino acid derivatives, using Huisgen's 1,3-dipolar cycloaddition method between an azide and substituted alkyne, giving rise to two regioisomers 1,4 and 1,5 under tedious heating conditions, with rather long reaction times [19][20][21]. The development of click chemistry, which allows 1,2,3-triazoles to be obtained in a simple and efficient way, has flooded the literature in recent years with their ability to affect the reactivity of biological targets and to influence metabolism and pharmacokinetics [22].…”