10341-26-1Relevant articles and documents
Novel Approach to Lactams via (Triisopropylsilyl)azidohydrin Formation and Photoinduced Schmidt Rearrangement
Evans, P. Andrew,Modi, Dilip P.
, p. 6662 - 6663 (1995)
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Mild, calcium catalysed Beckmann rearrangements
Kiely-Collins,Sechi,Brennan,McLaughlin
supporting information, p. 654 - 657 (2018/02/06)
A mild calcium catalysed Beckmann rearrangement has been realised, which forgoes the more traditional harsh reactions conditions associated with the transformation. The catalyst system is shown to be tolerant towards a wide variety of functional groups relevant to natural product synthesis and medicinal chemistry and the synthetic utility of the reaction has also been investigated. A preliminary mechanistic investigation was performed to understand the nature of the incoming nucleophile and a possible reaction pathway is described.
Remodeling and Enhancing Schmidt Reaction Pathways in Hexafluoroisopropanol
Motiwala, Hashim F.,Charaschanya, Manwika,Day, Victor W.,Aubé, Jeffrey
, p. 1593 - 1609 (2016/03/01)
The effect of carrying out two variations of the Schmidt reaction with ketone electrophiles in hexafluoroisopropanol (HFIP) solvent has been studied. When TMSN3 is reacted with ketones in the presence of triflic acid (TfOH) promoter, tetrazoles are obtained as the major products. This observation is in contrast to established methods, which usually lead to amides or lactams arising from formal NH insertion as the major products. The full product profiles of several examples of this reaction are also reported and found to include mechanistically interesting products (e.g., double ring expansion). Application of TfOH promoter in HFIP was also found to promote the reaction of a hydroxyalkyl azide with a ketone, which affords lactams following nucleophilic opening of initially formed iminium ether more efficiently than previously reported methods. (Chemical Equation Presented).
