The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction
A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reacti...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2017-01-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.10 |
| _version_ | 1818612331654938624 |
|---|---|
| author | Erika Bálint Ádám Tajti Anna Ádám István Csontos Konstantin Karaghiosoff Mátyás Czugler Péter Ábrányi-Balogh György Keglevich |
| author_facet | Erika Bálint Ádám Tajti Anna Ádám István Csontos Konstantin Karaghiosoff Mátyás Czugler Péter Ábrányi-Balogh György Keglevich |
| author_sort | Erika Bálint |
| collection | DOAJ |
| description | A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair. |
| first_indexed | 2024-12-16T15:44:32Z |
| format | Article |
| id | doaj.art-0eb03ff84c6f4a58b50468732c78f243 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T15:44:32Z |
| publishDate | 2017-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-0eb03ff84c6f4a58b50468732c78f2432022-12-21T22:25:50ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-01-01131768610.3762/bjoc.13.101860-5397-13-10The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reactionErika Bálint0Ádám Tajti1Anna Ádám2István Csontos3Konstantin Karaghiosoff4Mátyás Czugler5Péter Ábrányi-Balogh6György Keglevich7MTΑ-BME Research Group for Organic Chemical Technology, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment Chemie, Ludwig-Maximilians-Universität München, 81377 München, GermanyDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryHungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, 1519 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryA family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair.https://doi.org/10.3762/bjoc.13.10α-aryl-α-aminophosphine oxidesα-aryl-α-aminophosphonatesmicrowavePudovik reaction |
| spellingShingle | Erika Bálint Ádám Tajti Anna Ádám István Csontos Konstantin Karaghiosoff Mátyás Czugler Péter Ábrányi-Balogh György Keglevich The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction Beilstein Journal of Organic Chemistry α-aryl-α-aminophosphine oxides α-aryl-α-aminophosphonates microwave Pudovik reaction |
| title | The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction |
| title_full | The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction |
| title_fullStr | The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction |
| title_full_unstemmed | The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction |
| title_short | The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction |
| title_sort | synthesis of α aryl α aminophosphonates and α aryl α aminophosphine oxides by the microwave assisted pudovik reaction |
| topic | α-aryl-α-aminophosphine oxides α-aryl-α-aminophosphonates microwave Pudovik reaction |
| url | https://doi.org/10.3762/bjoc.13.10 |
| work_keys_str_mv | AT erikabalint thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT adamtajti thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT annaadam thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT istvancsontos thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT konstantinkaraghiosoff thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT matyasczugler thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT peterabranyibalogh thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT gyorgykeglevich thesynthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT erikabalint synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT adamtajti synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT annaadam synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT istvancsontos synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT konstantinkaraghiosoff synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT matyasczugler synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT peterabranyibalogh synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction AT gyorgykeglevich synthesisofaarylaaminophosphonatesandaarylaaminophosphineoxidesbythemicrowaveassistedpudovikreaction |