Journal of Heterocyclic Chemistry p. 663 - 670 (1996)
Update date:2022-08-03
Topics:
Kappe, Thomas
Schnell, Barbara
3-Aroyl-4-hydroxy-2-quinolones 4 and 11 can be synthesized starting with 1 or 9 via Fries rearrangement of the corresponding esters 3 and 10, catalyzed by potassium cyanide and 18-crown-6. A one pot procedure is presented in which the esters do not need to be isolated. Reduction of the aryl ketones 4 and 11 with zinc dust leads to the benzyl derivatives 5 and 12. Reaction of the aryl ketones 4 and 11 with hydroxylamine and subsequent heating of the crude product leads via thermal Beckmann rearrangement and dehydration to oxazoloquinolones 7 and 14. 2-Aroyloxypyrido[1,2-a]pyrimidin-4-ones 17 and 20 could not be converted to the corresponding ketones by Fries rearrangement.
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Doi:10.1016/0040-4039(96)01217-8
(1996)Doi:10.1021/ol0499203
(2004)Doi:10.1007/s00044-009-9202-z
(2010)Doi:10.1016/0040-4039(96)01586-9
(1996)Doi:10.1039/d0cc00480d
(2020)Doi:10.1021/jo951672o
(1996)