Between other applications oxazolidinones are largely used as intermediates as well as chiral auxiliaries in organic synthesis1 and constitute a class of new antibacterial and antibiotics,2-7 the best pharmaceutical performances are usually observed for N-aryl oxazolidin-2-ones (NAOs), such as Linezolid,8 Tedizolid9 and Toloxatone,10 that are FDA-approved drugs. One of the most interesting methodologies for the synthesis of NAOs is the CO2 cycloaddition to aziridines in order to use this greenhouse gas as a renewable C1 synthetic building block. Recently, we have reported a ruthenium porphyrin-based catalytic procedure for synthesising N alkyl oxazolidin-2-ones11,12 and, during our efforts to extend the same procedure to the synthesis of NAOs, we discovered that this reaction was efficiently promoted by the very convenient TPPH2/TBACl catalytic system (TPPH2=tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride). Here, we report the optimization and study scope of the synthesis of N aryl oxazolidin-2-ones, which were obtained either by reacting CO2 with purified N aryl aziridines or by applying a two-steps procedure. The latter methodology consists in the Ru(TPP)CO-catalysed synthesis of N-aryl aziridines that were converted into corresponding NAOs by the TPPH2/TBACl-catalysed cycloaddition of CO2. 1. Z. Vahideh and M. H. Majid, Current Organic Synthesis, 2018, 15, 3-20. 2. F. H. Malik Nasibullah, Naseem Ahmad, Abdul Rahman Khan, and Masihur Rahman, Adv. Sci. Eng. Med., 2015, 7, 91-111. 3. S. J. Pradeep, D. V. Maulikkumar, M. D. Tejas and K. C. Asit, Current Medicinal Chemistry, 2015, 22, 4379-4397. 4. A. Bhushan, N. J. Martucci, O. B. Usta and M. L. Yarmush, Expert Opinion on Drug Metabolism & Toxicology, 2016, 12, 475-477. 5. C. Roger, J. A. Roberts and L. Muller, Clinical Pharmacokinetics, 2018, 57, 559-575. 6. M. Nasibullah, F. Hassan, N. Ahmad, A. R. Khan and M. Rahman, Advanced Science, Engineering and Medicine, 2015, 7, 91-111. 7. K. Michalska, I. Karpiuk, M. Król and S. Tyski, Bioorg. Med. Chem., 2013, 21, 577-591. 8. A. Zahedi Bialvaei, M. Rahbar, M. Yousefi, M. Asgharzadeh and H. Samadi Kafil, J. Antimicrob. Chemother., 2017, 72, 354-364. 9. D. McBride, T. Krekel, K. Hsueh and M. J. Durkin, Expert Opinion on Drug Metabolism & Toxicology, 2017, 13, 331-337. 10. F. Moureau, J. Wouters, D. P. Vercauteren, S. Collin, G. Evrard, F. Durant, F. Ducrey, J. J. Koenig and F. X. Jarreau, European Journal of Medicinal Chemistry, 1992, 27, 939-948. 11. D. Carminati, E. Gallo, C. Damiano, A. Caselli and D. Intrieri, Eur. J. Inorg. Chem., 2018, 2018, 5258-5262. 12. D. Intrieri, C. Damiano, P. Sonzini and E. Gallo, J. Porphyrins Phthalocyanines, 2019, 23, 305-328.

The Catalytic efficiency of Free-Base Porphyrins in promoting the N-Aryl oxazolidinones synthesis / P. Sonzini, C. Damiano, D. Intrieri, E. Gallo. ((Intervento presentato al 12. convegno International School of Organometallic Chemistry tenutosi a Camerino nel 2019.

The Catalytic efficiency of Free-Base Porphyrins in promoting the N-Aryl oxazolidinones synthesis

P. Sonzini
Writing – Original Draft Preparation
;
C. Damiano
Supervision
;
D. Intrieri
Supervision
;
E. Gallo
Supervision
2019

Abstract

Between other applications oxazolidinones are largely used as intermediates as well as chiral auxiliaries in organic synthesis1 and constitute a class of new antibacterial and antibiotics,2-7 the best pharmaceutical performances are usually observed for N-aryl oxazolidin-2-ones (NAOs), such as Linezolid,8 Tedizolid9 and Toloxatone,10 that are FDA-approved drugs. One of the most interesting methodologies for the synthesis of NAOs is the CO2 cycloaddition to aziridines in order to use this greenhouse gas as a renewable C1 synthetic building block. Recently, we have reported a ruthenium porphyrin-based catalytic procedure for synthesising N alkyl oxazolidin-2-ones11,12 and, during our efforts to extend the same procedure to the synthesis of NAOs, we discovered that this reaction was efficiently promoted by the very convenient TPPH2/TBACl catalytic system (TPPH2=tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride). Here, we report the optimization and study scope of the synthesis of N aryl oxazolidin-2-ones, which were obtained either by reacting CO2 with purified N aryl aziridines or by applying a two-steps procedure. The latter methodology consists in the Ru(TPP)CO-catalysed synthesis of N-aryl aziridines that were converted into corresponding NAOs by the TPPH2/TBACl-catalysed cycloaddition of CO2. 1. Z. Vahideh and M. H. Majid, Current Organic Synthesis, 2018, 15, 3-20. 2. F. H. Malik Nasibullah, Naseem Ahmad, Abdul Rahman Khan, and Masihur Rahman, Adv. Sci. Eng. Med., 2015, 7, 91-111. 3. S. J. Pradeep, D. V. Maulikkumar, M. D. Tejas and K. C. Asit, Current Medicinal Chemistry, 2015, 22, 4379-4397. 4. A. Bhushan, N. J. Martucci, O. B. Usta and M. L. Yarmush, Expert Opinion on Drug Metabolism & Toxicology, 2016, 12, 475-477. 5. C. Roger, J. A. Roberts and L. Muller, Clinical Pharmacokinetics, 2018, 57, 559-575. 6. M. Nasibullah, F. Hassan, N. Ahmad, A. R. Khan and M. Rahman, Advanced Science, Engineering and Medicine, 2015, 7, 91-111. 7. K. Michalska, I. Karpiuk, M. Król and S. Tyski, Bioorg. Med. Chem., 2013, 21, 577-591. 8. A. Zahedi Bialvaei, M. Rahbar, M. Yousefi, M. Asgharzadeh and H. Samadi Kafil, J. Antimicrob. Chemother., 2017, 72, 354-364. 9. D. McBride, T. Krekel, K. Hsueh and M. J. Durkin, Expert Opinion on Drug Metabolism & Toxicology, 2017, 13, 331-337. 10. F. Moureau, J. Wouters, D. P. Vercauteren, S. Collin, G. Evrard, F. Durant, F. Ducrey, J. J. Koenig and F. X. Jarreau, European Journal of Medicinal Chemistry, 1992, 27, 939-948. 11. D. Carminati, E. Gallo, C. Damiano, A. Caselli and D. Intrieri, Eur. J. Inorg. Chem., 2018, 2018, 5258-5262. 12. D. Intrieri, C. Damiano, P. Sonzini and E. Gallo, J. Porphyrins Phthalocyanines, 2019, 23, 305-328.
Porphyrins; carbon dioxide; cycloaddition; oxazolidinones; aziridined; TBACl; green chemistry
Settore CHIM/06 - Chimica Organica
Settore CHIM/03 - Chimica Generale e Inorganica
Università di Camerino
The Catalytic efficiency of Free-Base Porphyrins in promoting the N-Aryl oxazolidinones synthesis / P. Sonzini, C. Damiano, D. Intrieri, E. Gallo. ((Intervento presentato al 12. convegno International School of Organometallic Chemistry tenutosi a Camerino nel 2019.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/830722
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