With the aim to obtain 2(3H)-benzoxazolinones and 2(3H)-benzothiazolinone derivatives, we synthesized new imide compounds 5a-c, 6c-d and 7a-d by treating their 6-amino precursors with succinic, maleic or phthalic anhydride. The microwave (MW)-assisted reaction provided them more efficiently than through the corresponding isolated amic acids. The same nucleophile reagents were used in a MW-assisted formylation to obtain new formamide products 8-11, that were detected as cis/trans forms by NMR analysis. The ratio was in favor of the cis isomer and affected by the solvent, as also supported by DFT calculations

Microwave-assisted synthesis of new imide-and formamide-derivatives of 2(3H)-benzoxazolinones and 2(3H)-benzothiazolinones / Seddiki, Khemissi; Yahia, Wassila; Liacha, Messaoud; Defant, Andrea; Sighel, Denise; Mancini, Ines. - In: ARKIVOC. - ISSN 1551-7004. - ELETTRONICO. - 2017:4(2017), pp. 315-329. [10.3998/ark.5550190.p009.926]

Microwave-assisted synthesis of new imide-and formamide-derivatives of 2(3H)-benzoxazolinones and 2(3H)-benzothiazolinones

Seddiki, Khemissi;Defant, Andrea;Sighel, Denise;Mancini, Ines
2017

Abstract

With the aim to obtain 2(3H)-benzoxazolinones and 2(3H)-benzothiazolinone derivatives, we synthesized new imide compounds 5a-c, 6c-d and 7a-d by treating their 6-amino precursors with succinic, maleic or phthalic anhydride. The microwave (MW)-assisted reaction provided them more efficiently than through the corresponding isolated amic acids. The same nucleophile reagents were used in a MW-assisted formylation to obtain new formamide products 8-11, that were detected as cis/trans forms by NMR analysis. The ratio was in favor of the cis isomer and affected by the solvent, as also supported by DFT calculations
4
Seddiki, Khemissi; Yahia, Wassila; Liacha, Messaoud; Defant, Andrea; Sighel, Denise; Mancini, Ines
Microwave-assisted synthesis of new imide-and formamide-derivatives of 2(3H)-benzoxazolinones and 2(3H)-benzothiazolinones / Seddiki, Khemissi; Yahia, Wassila; Liacha, Messaoud; Defant, Andrea; Sighel, Denise; Mancini, Ines. - In: ARKIVOC. - ISSN 1551-7004. - ELETTRONICO. - 2017:4(2017), pp. 315-329. [10.3998/ark.5550190.p009.926]
File in questo prodotto:
File Dimensione Formato  
Arkivoc2017t.pdf

accesso aperto

Descrizione: file pdf
Tipologia: Versione editoriale (Publisher’s layout)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 388.26 kB
Formato Adobe PDF
388.26 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11572/180536
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 2
social impact