Abstract
Regioselectivity in the intra-molecular Diels–Alder (IMDA) reaction of furfurylcitraconamic acids derived from N-benzylfurfurylamines and citraconic anhydride can be controlled by substituents located in the furan ring and by reaction conditions. Reactions conducted under kinetic conditions resulted in cycloaddition products having methyl and aminomethylene substituent in 1,3-relationship whereas under thermodynamic conditions, excepting in the case of the 3-methylsulfanyl group, the products rearranged to more stable cycloadducts in which the substituents are in 1,2-relationship. Product formation can be explained on the basis of frontier orbital interactions and steric considerations.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
