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TMSCL as a rate accelerating additive in acylations of amines with 5-(α- amino-α'-hydroxy)methylene meldrum's acids
Abstract
Aspects are presented of the acylation of amines, alcohols and thiols with 5-(α-amino- α'-hydroxy)methylene Meldrum's acids. We placed special emphasis on the acylation reaction of secondary amines with 5-(α-amino- α'-hydroxy)methylene Meldrum's acids, which, due to their basicity, caused problems concerning salt formation with a Meldrum acid derivative. We found that secondary amines, which react at the slowest rate and with a low yield with 5-(α-amino- α'-hydroxy)methylene Meldrum's acid, react quickly and with high yields with the same reagent in the presence 1 to 3 equivalents of TMSCl. Acylation with this derivative of Meldrum acid were optimized for such factors as: reaction temperature, solvent polarity and acidity of the environment. We have prepared a wide range of non-symmetrical malononic acid diamids, esters and thioesters of malonamic acid.
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
SYNTHETIC COMMUNICATIONS
no. 47,
pages 975 - 988,
ISSN: 0039-7911 - Language:
- English
- Publication year:
- 2011
- Bibliographic description:
- Janikowska K., Makowiec S.: TMSCL as a rate accelerating additive in acylations of amines with 5-(α- amino-α'-hydroxy)methylene meldrum's acids// SYNTHETIC COMMUNICATIONS. -Vol. 47, nr. iss. 7 (2011), s.975-988
- Verified by:
- Gdańsk University of Technology
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