Abstract
2-Phenylthiazolin-5-one (2b) was generated in situ and condensed with various aldehydes in CH2Cl2 (r.t./20 min.), to obtain the corresponding 4-alkylidene or arylidene products in good yields (68-81%). The reaction is catalyzed by basic lead acetate, and is equally successful with both aliphatic and aromatic aldehydes. This mild version of the classical Erlenmeyer azlactone synthesis is apparently enabled by the enhanced aromaticity of the thioazlactone anion intermediate.
Highlights
We have recently reported interesting mechanistic and synthetic findings on the classical Erlenmyer azlactone synthesis,[1] which remains a useful approach to the synthesis of α-amino acids.[2]
We have shown that the reaction is apparently facilitated by the aromaticity of the intermediate azlactone anion that is generated under the basic reaction conditions
We report a useful extension of the classical synthesis by employing a thioazlactone analog, its anion being expected to be even more aromatically stabilized than the parent azlactone
Summary
We have recently reported interesting mechanistic and synthetic findings on the classical Erlenmyer azlactone synthesis,[1] which remains a useful approach to the synthesis of α-amino acids.[2]. We report a useful extension of the classical synthesis by employing a thioazlactone analog, its anion being expected to be even more aromatically stabilized than the parent azlactone.
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