Synthesis and Reactions of iV-Acetyl-and N-(2-Chloroacetyl)-N-[(2E)-1-methylbut-2-en-1-yl]- 2-iodoanilines

摘要

The reaction of N-(l-methylbut-2-en-1-yl)-2-iodaniline with Ac2O or C1CH2C(O)C1 results in a mixture of syn- and anti-atropisomers of N-acetyl- and N-chloroacetyl-N-(l-methylbut-2-en-1-yl)-2-iodaniline in a ratio of 1:1. Ozonolysis of the latter followed by reduction with dimethyl sulfide in CH2Cl2 gives rise to the atropisomers mixture of 2-[N-(chloroacetyl)-N-(2-iodophenyl)]aminopropanal in a ratio of 1:3. When heated in boiling benzene, the mixture of atropoisomeric aldehydes reacts with triphenylphosphine to afford a mixture of 2-[(N-acetyl)-N-(2-iodophenyl)]aminopropanal atropisomers in 1:3 ratio.