On December 27, 2002, Swenson, Rolf E.; Sowin, Thomas J.; Zhang, Henry Q. published an article.COA of Formula: C12H14F3NO2 The title of the article was Synthesis of Substituted Quinolines Using the Dianion Addition of N-Boc-anilines and α-Tolylsulfonyl-α,β-unsaturated Ketones. And the article contained the following:
A short and versatile synthesis of substituted quinolines is provided. Alkylation of sodium tolylsulfinate with bromomethyl- or chloromethyl ketones generates β-keto sulfones, e.g., I. Knoevenagel condensation of the β-keto sulfones with an aldehyde provides α-tolylsulfonyl-α,β-unsaturated ketones, e.g., II. Michael addition of the dianion of N-Boc-anilines in the presence of CuCN and LiCl with the unsaturated ketone generates a 1,4-adduct, which after deprotection of the Boc group and thermal elimination of the tolyl sulfone provides the quinoline, e.g., III. The experimental process involved the reaction of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate(cas: 141940-37-6).COA of Formula: C12H14F3NO2
The Article related to sodium tolylsulfinate halomethyl ketone alkylation, keto sulfone preparation aldehyde knoevenagel condensation, unsaturated ketone tolylsulfonyl preparation aniline dianion michael addition elimination, quinoline preparation and other aspects.COA of Formula: C12H14F3NO2
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