A straightforward and efficient synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines 6-9 has been carried out in excellent overall yields through the ring opening of epoxides 1 with arylsulfonamides 2 and 3, followed by cyclization of the hydroysulfonamides 4 and 5 thus obtained. Both steps are carried out under solid-liquid phase transfer catalysis (SL-PTC) conditions using potassium carbonate and sodium hydroxide as bases. The procedure is feasible for the synthesis of non-racemic 2-substituted benzoxazines.

Straightforward synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines under solid-liquid phase transfer catalysis conditions / D. Albanese, D. Landini, V. Lupi, M. Penso. - In: INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH. - ISSN 0888-5885. - 42:4(2003), pp. 680-686.

Straightforward synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines under solid-liquid phase transfer catalysis conditions

D. Albanese
Primo
;
D. Landini
Secondo
;
2003

Abstract

A straightforward and efficient synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines 6-9 has been carried out in excellent overall yields through the ring opening of epoxides 1 with arylsulfonamides 2 and 3, followed by cyclization of the hydroysulfonamides 4 and 5 thus obtained. Both steps are carried out under solid-liquid phase transfer catalysis (SL-PTC) conditions using potassium carbonate and sodium hydroxide as bases. The procedure is feasible for the synthesis of non-racemic 2-substituted benzoxazines.
Settore CHIM/04 - Chimica Industriale
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

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/2434/188814
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 29
  • ???jsp.display-item.citation.isi??? 30
social impact