Tetrahedron

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

R Murali, HSP Rao, HW Scheeren

Index: Murali, Rajappa; Surya Prakash Rao; Scheeren, Hans W Tetrahedron, 2001 , vol. 57, # 15 p. 3165 - 3174

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Citation Number: 28

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 ...