Abstract
A new synthetic route to primary amides via N-tritylamides was developed. The initially formed N-tritylamides, derived from acylation of tritylamine by activated carboxylic acid derivatives, were deprotected with trifluoroacetic acid at room temperature to the desired primary amides in good yields.
Highlights
Amide formation is a fundamental reaction of great interest in organic chemistry
In the course of our ongoing interest in tritylamine reactions and its use for the preparation of primary amines, 11 we have designed the synthesis of primary amides from N-tritylamides, derived by aminotritylation of carboxylic acid derivatives with tritylamine, followed by trityl deprotection (Scheme 1)
Scheme 1 illustrates our synthetic route starting from the appropriate carboxylic acids or derivatives which were converted via their tritylamides into the corresponding primary amides
Summary
Amide formation is a fundamental reaction of great interest in organic chemistry. The development of efficient methods for the synthesis of amides remains a great challenge because of their importance in chemistry and biology, with a wide range of industrial and pharmaceutical applications and as valuable intermediates in organic synthesis. In the course of our ongoing interest in tritylamine reactions and its use for the preparation of primary amines, 11 we have designed the synthesis of primary amides from N-tritylamides, derived by aminotritylation of carboxylic acid derivatives with tritylamine, followed by trityl deprotection (Scheme 1). In order to establish a general, simple and effective method for the synthesis of carboxamides, we performed experiments on a range of carboxylic acids and derivatives, which were successfully converted to the corresponding primary amides (Table 1).
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