4502-10-7Relevant articles and documents
Goto et al.
, p. 1045 (1962)
One-pot oxidative hydrolysis-oxidative cleavage of 7-borylindoles enables access to: O -amidophenols and 4-acylbenzoxazoles
Anderson, Kirsty,Eastabrook, Andrew S.,Sperry, Jonathan
, p. 3559 - 3562 (2020/04/09)
7-Borylindoles undergo a one-pot oxidative-hydrolysis of the arylboronate and oxidative cleavage of the indole C2-C3 double bond to afford o-amidophenol derivatives. Subsequent cyclisation delivers benzoxazoles bearing an acyl group at C4, a substitution pattern common to fungal-derived benzoxazole alkaloids. Using 7-borylindoles as substrates to access functionalised o-amidophenols circumvents the difficult preparation of these compounds from arenes, streamlining access to substituted 4-acylbenzoxazoles in the process.
Biomimetic Synthesis of 4-Acetylbenzoxazolin-2(3H)-one Isolated from Zea mays
Escobar, Carlos A.,Kluge, Michael,Sicker, Dieter
, p. 1407 - 1414 (2007/10/03)
4-Acctylbenzoxazolin-2(3H)-one has been prepared biomimetically during attempts to synthesize the hemiacetalic hydroxamic acid 5-acetyl-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one by the immediate degradation of this unstable compound generated as an intermediate. Thus, 4-acetylbenzoxazolin-2(3H)one recently isolated from Zea mays kernels, and similar to other benzoxazolin-2(3H)-ones known from plant sources, is assumed to have originated from the degradation of natural 5-acetyl-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one which in turn could have been enzymatically released by a β-glucosidase from the corresponding 2-β-D-glucoside.