90055-47-3Relevant articles and documents
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
Multicomponent reactions as a powerful tool for generic drug synthesis
Kalinski, Cedric,Lemoine, Hugues,Schmidt, Juergen,Burdack, Christoph,Kolb, Juergen,Umkehrer, Michael,Ross, Guenther
scheme or table, p. 4007 - 4011 (2009/05/27)
Multicomponent reactions (MCRs) are not only a powerful tool for drug discovery, they also represent an excellent methodology for synthesis rationalization. Here we wish to illustrate the potential of MCRs in the production of generic drugs by synthesizing, in racemic form, the antiplatelet agent clopidogrel and the nonsteroidal antiandrogen bicalutamide, using Ugi, Petasis and Passerini reactions. Georg Thieme Verlag Stuttgart.
2-thienylglycidic derivative, process for its preparation and its use as synthesis intermediate
-
, (2008/06/13)
The invention relates to isopropyl 2-thienylglycidate of formula: STR1 obtained by reaction of 2-thienylcarboxaldehyde with an isopropyl haloacetate. It is employed as a synthesis intermediate in the preparation of 2-thienylacetaldoxime and of medications derived from thieno[3,2-c]pyridine.