Microwave-assisted synthesis of N,N-bis(phosphinoylmethyl)amines and N,N,N-tris(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms

• Erika Bálint,
• Anna Tripolszky,
• László Hegedűs and
• György Keglevich

Beilstein J. Org. Chem. 2019, 15, 469–473, doi:10.3762/bjoc.15.40

• phosphorus atoms was synthesized by the microwave-assisted and catalyst-free Kabachnik–Fields reaction of (aminomethyl)phosphine oxides with paraformaldehyde and diphenylphosphine oxide. The three-component condensation of N,N-bis(phosphinoylmethyl)amine, paraformaldehyde and a secondary phosphine oxide

• affording N,N,N-tris(phosphinoylmethyl)amine derivatives was also elaborated. This method is a novel approach for the synthesis of the target products. Keywords: (aminomethyl)phosphine oxides; Kabachnik–Fields reaction; ligand; microwave; N,N-bis(phosphinoylmethyl)amines; N,N,N-tris(phosphinoylmethyl

• of alkylphenylphosphine oxides and the corresponding aldimine derivatives of thiazole 1 (Scheme 1) [12]. Cherkasov and his group applied the Kabachnik–Fields reaction to synthesize a P-chiral aminophosphine oxide with a 2-pyridyl substituent 3 (Scheme 2) [13]. Bis(aminophosphine oxide) derivatives

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• better yields than in protic solvents. When diethyl (2-oxopropyl)phosphonate and 4-nitrobenzaldehyde were treated in the presence of 50 mol % TsOH in acetonitrile, 5-phosphonato-3,4-dihydropyrimidin-2-one 18 was obtained in excellent yield (Scheme 5). 2 Kabachnik−Fields reaction and its post-condensation

• modifications The one-pot three-component reaction between aldehydes 19 (or ketones), amines 20 and dialkyl phosphonates 21 to afford α-aminophosphonates 22 is traditionally known as the Kabachnik–Fields reaction. This reaction was first reported in 1952 by Kabachnik, Medved and Fields (Scheme 6) [29][30]. Due

• to their wide range of biological activities, α-aminophosphonates have been extensively investigated and several reviews about their syntheses through the Kabachnik–Fields reaction have been reported [31][32][33]. However, an important feature of this reaction is that it provides an efficient route

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• conditions to prepare N-(pyren-1-ylidene)-tert-butylamine (1j) and dimethyl N-(tert-butyl)amino(pyren-1-yl)methylphosphonate (3Aj) via the aza-Pudovik reaction, the Kabachnik–Fields reaction was used as an alternative method [23]. The three-component reaction without any catalyst was carried out first in

• (3Ai) was obtained, when the Kabachnik–Fields reaction was carried out in the presence of a catalytic amount of trifluoroacetic acid in refluxing acetonitrile. The same procedure, i.e., the Kabachnik–Fields reaction in the presence of trifluoroacetic acid, but in refluxing methanol has been

• attributed to each nucleus. Compounds were also characterized by melting point measurements. Jayaprakash et al. [9] reported the synthesis of several pyrene-derived aminophosphonates via a silica-catalyzed Kabachnik–Fields reaction. Among others, they synthesized three amino-phosphonates 3Bb–d, reporting

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• group has developed the synthesis of D-glucopyranose-derived counterparts of compounds 25 and 26 [73]. The formation of an intermediate imine from a sugar azide and an aldehyde by Staudinger/aza-Wittig reaction was the key step of the synthesis. 2. The Kabachnik–Fields reaction The Kabachnik–Fields

• . An example of the application of the Kabachnik–Fields reaction in nucleoside chemistry represents the preparation of α-arylaminophosphonates 28 and 29 by Zhang et al. (Scheme 12) [76]. The reactions between 5-formyl-2'-deoxyuridine 27 (or its 3',5'-di-O-acetyl derivative 14), an aniline and dimethyl

• . Reagents and reaction conditions: i. a. 37% aq HCl, MeOH; b. NaOAc, 1,4-dioxane, H2O, 100 °C, overnight. Reagents and reaction conditions: i. DMAP, DCC, MeOH, rt, 1 h. The Kabachnik–Fields reaction. Reagents and reaction conditions: i. 60 °C, 3 h; ii. 80 °C, 2 h. The four-component Ugi reaction. Reagents

Phosphinate-containing heterocycles: A mini-review

• Olivier Berger and
• Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

• malonate anion. Tandem hydrophosphinylation/Michael/Michael reaction of allenyl-H-phosphinates. 5-Membered “cyclo-PALA” via intramolecular Mitsunobu reaction. 6-Membered “cyclo-PALA” via intramolecular Mitsunobu reaction. Intramolecular Kabachnik–Fields reaction. Tandem Kabachnik–Fields/alkylation reaction

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

• Natalia V. Pavlenko,
• Tatiana I. Oos,
• Yurii L. Yagupolskii,
• Igor I. Gerus,
• Uwe Doeller and
• Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

• overnight, argon atmosphere, mixture 3:4 ~ 10:1, ~70%. Three-component Kabachnik–Fields reaction of CF3(H)P(O)(OiPr) (2) with formaldehyde and dibenzylamine. Reagents and conditions: i) an equimolar mixture of reagents, H2O, 80 °C, 3 h, argon atmosphere, yield 10 ~80% or an equimolar mixture of reagents