Synthesis of Diels-Alder Bis-Adducts of Methoxycarbonyl-1,4-benzoquinone

Abstract

The feasibility of obtaining bis-adducts from a mono-substituted 1,4-benzoquinone with an electron withdrawing substituent, like methoxycarbonyl-1,4-benzoquinone with simple dienes such as 1,3- butadiene and cyclopentadiene were investigated and a procedure for the preparation of 9,10-anthraquinones was established. The bisadducts were obtained in a moderate yield, around 35 %.