Chemistry of 5-oxodihydroisoxazoles. Part 18.1 Synthesis of oxazoles by the photolysis and pyrolysis of 2-acyl-5-oxo-2, 5-dihydroisoxazoles
RH Prager, JA Smith, CM Williams
Index: Prager, Rolf H.; Smith, Jason A.; Weber, Ben; Williams, Craig M. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 17 p. 2665 - 2672
Full Text: HTML
Citation Number: 48
Abstract
N-Acylisoxazol-5-ones lose carbon dioxide under photochemical and thermal conditions affording iminocarbenes which undergo intramolecular cyclisation through the oxygen of the acyl group to give oxazoles. Under photochemical conditions those acylisoxazolones with electron withdrawing groups at C-4 usually give high yields of oxazoles, while those with electron donating groups at C-4 give only poor yields: the reverse is observed under ...
Related Articles:
Pummerer reaction methodology for the synthesis of 5-thiophenyl substituted oxazoles
[Kreisberg, Jennifer D; Magnus, Philip; Shinde, Shirin Tetrahedron Letters, 2002 , vol. 43, # 41 p. 7393 - 7396]
Synthese de pyrroles et d'oxazoles par pyrolyse de N-(hydroxy-2′ ethyl) amino-3 propenoate
[Pale-Grosdemange, Catherine; Chuche, Josselin Tetrahedron, 1989 , vol. 45, # 11 p. 3397 - 3414]
Pummerer reaction methodology for the synthesis of 5-thiophenyl substituted oxazoles
[Kreisberg, Jennifer D; Magnus, Philip; Shinde, Shirin Tetrahedron Letters, 2002 , vol. 43, # 41 p. 7393 - 7396]
The synthesis of oxazoles by thermolysis or photolysis of 2-acylisoxazol-5-ones
[Ang, Kiah H.; Prager, Rolf H.; Smith, Jason A.; Weber, Ben; Williams, Craig M. Tetrahedron Letters, 1996 , vol. 37, # 5 p. 675 - 678]
Synthese de pyrroles et d'oxazoles par pyrolyse de N-(hydroxy-2′ ethyl) amino-3 propenoate
[Pale-Grosdemange, Catherine; Chuche, Josselin Tetrahedron, 1989 , vol. 45, # 11 p. 3397 - 3414]