Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Abstract

Terephthalic acid hydrazide (1) wasreacted with phenylphosphonic dichloride to yield bis (1,3,4,2-oxadiazaphosphole) derivative 3, which was condensed with α-aminophosphonic acid derivative 4 to afford bis [(1,2,4,3-triazaphospholyl) (chromonyl)methylphosphonic acid] derivative 5. The addition of diethyl phosphite to Schiff bases 9 and 10 derived from the

5-Methyl-3,8-di-(2-amino-4-bromophenyl)-4,9-dioxa-1,2,6,7-tetraaza-5λ5-phosphaspiro[4.4]nona-2,7-diene

“…reported by Schmidpeter [10] and their synthesis has been more recently investigated by Gholivand [11] and Hua [12]. Similar condensations between aromatic dihydrazides and phosphonyl dichlorides were also published by Ali [13]. In previous reports, only simple aromatic hydrazides were condensed with phosphonyl dichlorides, which limited further modifications of obtained products.…”

“…Melting points are uncorrected and were measured on a Büchi (New Castle, DE, USA) Melting Point B-540 apparatus. The 1 H, 13 C and 31 P-NMR spectra in CDCl3 were recorded at the Department of Chemistry, Warsaw University, using a Bruker AVANCE III HD (Billerica, MA, USA) 500 MHz spectrometer; shift values in parts per million are relative to the SiMe4 internal reference. The resonance assignments are based on a peak integration, peak multiplicity, and 2D correlation experiments.…”

“…The resulting yellow crystals were washed with methanol to give a white powder. Supplementary Materials: Copies of the 1 H-NMR, 13 C-NMR, dept135, 31 P-NMR, IR, HRMS-ESI mass spectra are available online at http://www.mdpi.com/1422-8599/2018/1/M978/s1.…”

Methods for the synthesis of α-heterocyclic/heteroaryl-α-aminophosphonic acids and their esters

“…To our knowledge, there are several methods for the synthesis of α-heterocyclic/heteroaryl α-aminophosphonates ( Figure 1). In connection with our work on the preparation of α-aminophosphonates containing heterocyclic systems, [16][17][18][19] we report in this review article all the available synthetic methods of α-heterocyclic/heteroaryl α-aminophosphonates which were published until 2013. …”

Vilsmeier-Haack Reaction of Phosphonic Dihydrazide: Synthesis of 4- {[(Dimethyl)azanylidenonium Chloride] Methyl} Amino-2,3-Dihydro-3-Oxo-4<i>H</i>-1,2,4, 3-Triazaphosphole

“…On the other hand, phosphorus heterocycles containing nitrogen heteroatoms adjacent to phosphorus atom exh ibited interesting biological properties [6,7]. As a part of our search for new expected biologically active phosphorus heterocycles [8][9][10][11], we are interested in introducing such N−P−N pattern into heterocyclic structure by applying the Vils meier Haack reaction on phosphonic dihydrazide. To the best of our knowledge, the synthesis of phosphorus heterocycles by the Vilsmeier reagent has not been reported in literature.…”