A Convenient Procedure for the Formylation of Amines and Alcohols Using Cyanomethyl Formate
- 1 June 1993
- journal article
- research article
- Published by Informa UK Limited in Synthetic Communications
- Vol. 23 (11), 1561-1568
- https://doi.org/10.1080/00397919308011251
Abstract
A simple method for the direct formylation of amines using cyanomethyl formate is described. The formylation succeeds in moderate to high yields under mild and neutral conditions. Thus, formamides 2a-f, 2i-m are obtained at room temperature. A chemoselective N-formylation is achieved in the case of ethanolamine. The formylation of nitroanilines and the O-formylation of alcohols only succeeds in the presence of a catalytic amount of imidazole leading to 2g,h and 3a-e, respectively.Keywords
This publication has 16 references indexed in Scilit:
- A New Formylating Reagent:N-(Diethylcarbamoyl)-N-methoxyformamideSynthesis, 1992
- An Improved Procedure forN-Formylation of Secondary Amines Using Chlorotrimethylsilane-Imidazole-N,N-DimethylformamideSynlett, 1992
- Enol formates: ruthenium catalysed formation and formylating reagentsJournal of the Chemical Society, Perkin Transactions 1, 1991
- Trimethylsilyl Esters: Temporary Protection of Carboxylic Acids During Hydroboration ReactionsSynthetic Communications, 1989
- A Novel Synthetic Route to 2-Aryl-2H-Benzotriazole 1-OxidesSynthetic Communications, 1989
- Formylating agentsChemical Reviews, 1987
- Electrophilic Reagents—Recent Developments and Their Preparative ApplicationAngewandte Chemie-International Edition, 1980
- Heterocyclische Amide der AmeisensäureEuropean Journal of Organic Chemistry, 1962
- The Conversion of Formamides into Formamidines1Journal of the American Chemical Society, 1954
- Physikalisch‐chemische Untersuchungen bei organischen Säureamiden (Constitution der Nitrosoalkylurethane, der Säureamide, des Anthranils, Siedepunktsregelmässigkeiten bei Säureamiden, Analogie der Formylamine und Nitrosamine)European Journal of Inorganic Chemistry, 1903