One-pot synthesis and conformational features of n,n'-disubstituted ketene aminals |
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Authors: | Shi Yan Zhang Jing Grazier Nyeemah Stein Philip D Atwal Karnail S Traeger Sarah C Callahan Sharon P Malley Mary F Galella Michael A Gougoutas Jack Z |
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Institution: | The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 5400, Princeton, New Jersey 08543-5400, USA. yan.shi@bms.com |
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Abstract: | N,N'-Disubstituted ketene aminals are bioisosteres of thioureas and are useful building blocks in many synthetic operations. A convenient one-pot synthesis of N,N'-disubstituted ketene aminals from activated methylene compounds and isothiocyanates is described. Most of these aminals exist in rotameric equilibrium around the central C=C bonds in solution, and the rotamers are stabilized by intramolecular hydrogen bonding both in solution and in solid states. |
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