Synthesis of Coumarins, 4-Hydroxycoumarins, and 4-Hydroxyquinolinones by Tellurium-Triggered Cyclizations1
DC Dittmer, Q Li, DV Avilov
Index: Dittmer, Donald C.; Li, Qun; Avilov, Dimitry V. Journal of Organic Chemistry, 2005 , vol. 70, # 12 p. 4682 - 4686
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Citation Number: 57
Abstract
Coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolin-2 (1 H)-ones can be conveniently prepared by treatment of α-halocarboxylic acid esters of salicylaldehyde, o- hydroxyacetophenone, methyl salicylate, and methyl N-methyl-or N-phenylanthranilates with sodium or lithium telluride. Phenylketene formation competes with cyclization of the α- chlorophenylacetate ester of methyl salicylate as demonstrated by a trapping experiment ...
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