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One‐Pot Sequential Schmidt and Ritter Reactions for the Synthesis of N ‐ tert ‐Butyl Amides
Author(s) -
Hazarika Nabajyoti,
Baishya Gakul
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402662
Subject(s) - ritter reaction , chemistry , schmidt reaction , reagent , nitrile , organic chemistry , acetic acid , substrate (aquarium) , catalysis , oceanography , geology
The first example of the direct conversion of benzaldehydes into their corresponding N ‐ tert ‐butyl amides through a Schmidt reaction/Ritter reaction sequence is described. A reagent mixture consisting of NaN 3 and HBF 4 · OEt 2 in acetic acid efficiently reacts with aromatic and conjugated (α,β‐unsaturated) aldehydes to produce nitrile derivatives, which in situ undergo a Ritter reaction with tert ‐butyl acetate to afford the corresponding N ‐ tert ‐butyl amides in almost quantitative yields. The method needs no column chromatography purification. The wide substrate scope as well as the ready availability of the reagent system also make this protocol convenient.