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Synthesis 2015; 47(18): 2851-2859
DOI: 10.1055/s-0034-1380754
DOI: 10.1055/s-0034-1380754
paper
Practical Synthesis of N-(Diphenylmethyl)- and N-(1-Adamantyl)amides Directly from Aldehydes via a One-Pot Schmidt and Ritter Reaction Sequence
Further Information
Publication History
Received: 04 March 2015
Accepted after revision: 16 April 2015
Publication Date:
23 June 2015 (online)
Abstract
Nonoxidative and noncoupling reaction conditions have been developed for the synthesis of N-(diphenylmethyl)- and N-(1-adamantyl)amide derivatives directly from aldehydes by employing the concept of a Schmidt and Ritter reaction sequence in a one-pot operation. The reagent mixture consisting of sodium azide and HBF4·OEt2 in acetic acid converts the aldehydes into their respective nitrile analogues which in situ undergo the Ritter reaction with diphenylmethanol or 1-adamantanol to afford the corresponding N-(diphenylmethyl)- or N-(1-adamantyl)amide derivatives in very good yields. The method does not require column chromatographic purification for isolation of the products. With its simple reaction procedure and easy product purification technique, this method outshines earlier conventional two-step methods.
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