Literature DB >> 33923090

Synthesis of α-Aminophosphonates and Related Derivatives; the Last Decade of the Kabachnik-Fields Reaction.

Petra R Varga1, György Keglevich1.   

Abstract

The Kabachnik-Fields reaction, comprising the condensation of an amine, oxo compound and a P-reagent (generally a >P(O)H species or trialkyl phosphite), still attracts interest due to the challenging synthetic procedures and the potential biological activity of the resulting α-aminophosphonic derivatives. Following the success of the first part (Molecules 2012, 17, 12821), here we summarize the synthetic developments in this field accumulated in the last decade. The procedures compiled include catalytic accomplishments as well as catalyst-free and/or solvent-free "greener" protocols. The products embrace α-aminophosphonates, α-aminophosphinates, and α-aminophosphine oxides along with different bis derivatives from the double phospha-Mannich approach. The newer developments of the aza-Pudovik reactions are also included.

Entities:  

Keywords:  Kabachnik–Fields reaction; aza-Pudovik reaction; bis derivatives; catalysts; green methods; phospha-Mannich reaction; α-aminophosphine oxides; α-aminophosphonates

Year:  2021        PMID: 33923090     DOI: 10.3390/molecules26092511

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  16 in total

Review 1.  Aminophosphonic acids of potential medical importance.

Authors:  P Kafarski; B Lejczak
Journal:  Curr Med Chem Anticancer Agents       Date:  2001-11

2.  PEG-SO(3)H catalyzed synthesis and cytotoxicity of α-aminophosphonates.

Authors:  C Bhupendra Reddy; K Suresh Kumar; M Anil Kumar; M Veera Narayana Reddy; B Satheesh Krishna; M Naveen; M K Arunasree; C Suresh Reddy; C Naga Raju; C Devendranath Reddy
Journal:  Eur J Med Chem       Date:  2011-11-20       Impact factor: 6.514

3.  Design, synthesis and biological evaluation of novel α-aminophosphonate oxadiazoles via optimized iron triflate catalyzed reaction as apoptotic inducers.

Authors:  Ewies F Ewies; Marwa El-Hussieny; Naglaa F El-Sayed; Marwa A Fouad
Journal:  Eur J Med Chem       Date:  2019-07-11       Impact factor: 6.514

4.  Aminobisphosphonate Polymers via RAFT and a Multicomponent Kabachnik-Fields Reaction.

Authors:  Patricia R Bachler; Michael D Schulz; Chelsea A Sparks; Kenneth B Wagener; Brent S Sumerlin
Journal:  Macromol Rapid Commun       Date:  2015-03-24       Impact factor: 5.734

Review 5.  Recent synthesis of aminophosphonic acids as potential biological importance.

Authors:  Emilia D Naydenova; Petar T Todorov; Kolio D Troev
Journal:  Amino Acids       Date:  2009-02-20       Impact factor: 3.520

6.  Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation.

Authors:  Erika Bálint; Ádám Tajti; Anna Dzielak; Gerhard Hägele; György Keglevich
Journal:  Beilstein J Org Chem       Date:  2016-07-19       Impact factor: 2.883

7.  Microwave-Assisted Kabachnik⁻Fields Reaction with Amino Alcohols as the Amine Component.

Authors:  Ádám Tajti; Enikő Szatmári; Franc Perdih; György Keglevich; Erika Bálint
Journal:  Molecules       Date:  2019-04-25       Impact factor: 4.411

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

Authors:  Erika Bálint; Anna Tripolszky; László Hegedűs; György Keglevich
Journal:  Beilstein J Org Chem       Date:  2019-02-15       Impact factor: 2.883

9.  Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates.

Authors:  Maheshwara Reddy Nadiveedhi; Poojith Nuthalapati; Mohan Gundluru; Mohan Reddy Yanamula; Saritha Venkatareddy Kallimakula; Visweswara Rao Pasupuleti; Vijaya Kumar Reddy Avula; Swetha Vallela; Grigory Vasilievich Zyryanov; Satheesh Krishna Balam; Suresh Reddy Cirandur
Journal:  ACS Omega       Date:  2021-01-21

10.  Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety.

Authors:  Ismahene Bazine; Samira Bendjedid; Abbes Boukhari
Journal:  Arch Pharm (Weinheim)       Date:  2020-12-07       Impact factor: 4.613

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  6 in total

Review 1.  Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications.

Authors:  Babak Kaboudin; Payam Daliri; Samaneh Faghih; Hesam Esfandiari
Journal:  Front Chem       Date:  2022-06-01       Impact factor: 5.545

2.  Novel α-Aminophosphonates and α-Aminophosphonic Acids: Synthesis, Molecular Docking and Evaluation of Antifungal Activity against Scedosporium Species.

Authors:  Anthonny Cordero-Díaz; Efren Robledo-Leal; Eugenio Hernández-Fernández; Emanuel Hernández-Núñez; Mariana Elizondo-Zertuche; Susana T López-Cortina
Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927

3.  Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik-Fields Reaction.

Authors:  Dominik Koszelewski; Paweł Kowalczyk; Paweł Śmigielski; Jan Samsonowicz-Górski; Karol Kramkowski; Aleksandra Wypych; Mateusz Szymczak; Ryszard Ostaszewski
Journal:  Materials (Basel)       Date:  2022-05-27       Impact factor: 3.748

4.  Molecular Environment Effects That Modulate the Photophysical Properties of Novel 1,3-Phosphinoamines Based on 2,1,3-Benzothiadiazole.

Authors:  Radmir M Khisamov; Alexey A Ryadun; Sergey N Konchenko; Taisiya S Sukhikh
Journal:  Molecules       Date:  2022-06-16       Impact factor: 4.927

Review 5.  Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks.

Authors:  César A Godoy; Juan S Pardo-Tamayo; Oveimar Barbosa
Journal:  Int J Mol Sci       Date:  2022-09-01       Impact factor: 6.208

6.  Facile Conversion of α-Amino Acids into α-Amino Phosphonates by Decarboxylative Phosphorylation using Visible-Light Photocatalysis.

Authors:  Dominik Reich; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-04       Impact factor: 16.823

  6 in total

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