- An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
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A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
- Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 1990 - 1995
(2017/06/09)
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- Facile preparation of pyrimidinediones and thioacrylamides: Via reductive functionalization of amides
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The development of an efficient protocol for the reductive functionalization of amides into pyrimidinediones and amino-substituted thioacrylamides is presented. Enamines are generated in a highly chemoselective amide hydrosilylation reaction catalyzed by
- Trillo, Paz,Slagbrand, Tove,Tinnis, Fredrik,Adolfsson, Hans
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supporting information
p. 9159 - 9162
(2017/08/17)
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- Transformation of Amides into Highly Functionalized Triazolines
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Triazoles and triazolines are important classes of heterocyclic compounds known to exhibit biological activity. Significant focus has been given to the development of synthetic approaches for the preparation of triazoles, and they are today easily obtainable through a large variety of protocols. The number of synthetic procedures for the formation of triazolines, on the other hand, is limited and further research in this field is required. The protocol presented here gives access to a broad scope of 1,4,5-substituted 1,2,3-triazolines through a one-pot transformation of carboxamides. The two-step procedure involves a Mo(CO)6-catalyzed reduction of tertiary amides to afford the corresponding enamines, followed by in situ cycloaddition of organic azides to form triazolines. The amide reduction is chemoselective and allows for a wide variety of functional groups such as esters, ketones, aldehydes, and imines to be tolerated. Furthermore, a modification of this one-pot procedure gives access to the corresponding triazoles. The chemically stable amide functionality is demonstrated to be an efficient synthetic handle for the formation of highly substituted triazolines or triazoles.
- Slagbrand, Tove,Volkov, Alexey,Trillo, Paz,Tinnis, Fredrik,Adolfsson, Hans
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p. 1771 - 1775
(2017/08/09)
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- NEW HETEROCYCLIC DERIVATIVES USEFUL FOR THE TREATMENT OF CNS DISORDERS
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The present invention relates to new compounds, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals.
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Page/Page column 72
(2008/12/08)
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