An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne.
An efficient synthesis of a range of 1,2-benzisoxazoles using an improved 1,3-dipolar cycloaddition of nitrile oxides and benzyne is described. Key to the procedure is the in situ generation of the reactive nitrile oxide and benzyne reaction partners mediated by TBAF. Reactions are complete within 30 s, giving the target products in good to excellent yield.
Spiteri
Christian
C
School of Chemistry, University of Nottingham, University Park, Nottingham, UK NG7 2RD.
Sharma
Pallavi
P
Zhang
Fengzhi
F
Macdonald
Simon J F
SJ
Keeling
Steve
S
Moses
John E
JE
D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry
C441200:1,2-benzisoxazole; D001555:Benzene Derivatives; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides; C524146:benzyne