Highly efficient metal-free one-pot synthesis of α-aminophosphonates through reduction followed by Kabachnik–fields reaction using three-component system

Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: redox properties in the fast synthesis of N-arylacetamides and indolo(pyrrolo)[1,2-a]quinoxalines

“…[7][8][9] They are also fundamental building blocks employed in the synthesis of amines which are obtained by the reduction of the nitro group through metalacid combinations, catalytic hydrogenation, hydride transfer reductions, catalytic transfer hydrogenation and metal-free reduction methods. 10 The synthetic utility of this transformation is highlighted in several one pot procedures for the obtention of diverse structures including imines, amides 11 and a-aminophosphonates 12 together with heterocyclic compounds such as benzimidazoles, [13][14][15] quinazolinones, 16,17 pyrrolines, 18 isoindolinone derivatives, 19 tetrahydroquinolines, [20][21][22][23] and quinoxalines, 24,25 where a tandem one-pot reduction and intramolecular cyclization reaction is achieved.…”

Photo-Oxidation Coupled Kabachnik–Fields and Bigenelli Reactions for Direct Conversion of Benzyl alcohols to α-Aminophosphonates and Dihydropyrimidones

“…The aminophosphonates can also be synthesised via acid-catalyzed (Lewis/ Brønsted), 6,7 catalyst-free, 8 microwave assisted 9 condensation of H-phosphonates with aldehydes or imines. Furthermore, synthesis of α-aminophosphonates has also been achieved from substrates other than aldehydes using methylene aziridines, 10 dehydrogenative α-phosphonation of substituted N,N-dialkylanilines, 11 reduction of aryl nitro compounds, 12 reductive phosphination of amides, 13 and biomass-derived hydroxyl methyl furfural. 14 As such, we were particularly intrigued to explore the feasibility of ubiquitously available benzyl alcohols as substrates for the synthesis of α-aminophosphonates.…”