One-pot synthesis and conformational features of n,n'-disubstituted ketene aminals.
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.
Shi
Yan
Y
The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 5400, Princeton, New Jersey 08543-5400, USA. yan.shi@bms.com
Zhang
Jing
J
Grazier
Nyeemah
N
Stein
Philip D
PD
Atwal
Karnail S
KS
Traeger
Sarah C
SC
Callahan
Sharon P
SP
Malley
Mary F
MF
Galella
Michael A
MA
Gougoutas
Jack Z
JZ