Chandrasekhar, Sosale and Srimannarayana, Malempati (2009) The Erlenmeyer synthesis with a thioazlactone. In: ARKIVOC (Part 1). pp. 290-295.
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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.
|Item Type:||Journal Article|
|Additional Information:||Copyright for this article belongs to ARKAT USA INC.|
|Keywords:||Amino acid; aromaticity; Erlenmeyer; lead acetate; thioazlactone|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||27 Jan 2010 09:53|
|Last Modified:||19 Sep 2010 05:54|
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