
TY  - JOUR
A1  - Brewer, JD 
A1  - Davidson, WJ 
A1  - Elix, JA 
A1  - Leppik, RA 
T1  - Annelated furans. VI. Diels-Alder addition to 3-Methoxy-2-vinylbenzofurans
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1971
VL  - 24
IS  - 9
SP  - 1883
EP  - 1898
KW  - 
UR  - https://doi.org/10.1071/CH9711883 
N2  - The Diels-Alder addition of 3-methoxy-2-vinylbenzofurans to acetylenic dienophiles has been shown to be accompanied by elimination of methanol, thus affording a direct route to polyfunctional dibenzofurans. Ethylenic dienophiles also reacted but the nature of the product varied with the dienophile: thus tetra-cyanoethylene and 2- isopropenyl-3-methoxybenzofuran (17) gave the simple 1 : 1 adduct, 1,1,2,2-tetracyano-11-methoxy-4-methyl-1,2,3,11-tetrahydrodibenzofuran (26), while addition of maleic anhydride to (17) was accompanied by elimination of methanol to form the 1,2-dihydrodibenzofuran, 4-methyl- 1,2-dihydrodibenzofuran-1,2-dicarboxylic acid anhydride (27).     The addition of p-benzoquinone and 1,4-naphthaquinone to (17) gave the polycyclic quinones, 6-methyl-1,4-dioxo-1,4- dihydrobenzo[b]naphtho[1,2-d]furan (28) and 7-methyl-5,13-dioxo-5,13- dihydrobenzo[b]anthra[1,2-d]furan (29) respectively.     The methylation of enolic 3-hydroxybenzofurans has also been studied. 
ER  -

