Intra-molecular Diels–Alder reactions of citraconamic acids from furfurylamines and citraconic anhydride: effects of substitution in the furan ring on regioselectivity

Add time:07/15/2019    Source:sciencedirect.com

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.

We also recommend Trading Suppliers and Manufacturers of 2-(methylsulfanyl)furan (cas 13129-38-9). Pls Click Website Link as below: cas 13129-38-9 suppliers

Prev:Investigation of THF (cas 634-19-5) hydrate formation kinetics: Experimental measurements of volume changes
Next:One-pot synthesis of amino-functionalized ethylene carbonates under atmospheric pressure of CO2)