Reactions of an o-Quinone Monoimide with 1,3,5-Trimethoxybenzene, 2-Methoxythiophene, 2-Methoxyfuran, and 1-Methyl, 2-Methyl-, and 1,2-Dimethylindoles

Article abstract of DOI:10.1021/jo00377a017

The o-quinone monoimide 1 reacts with the electron-rich aromatic reagents 1,3,5-trimethoxybenzene, 2-methoxythiophene, and 1-methyl-, 2-methyl-, and 1,2-dimethylindoles to give the N-2,4-dichloro-6-hydroxyphenyl derivatives of N-(2,4,6-trimethoxyphenyl)-, N-(5-methoxy-2-thienyl)-, N-(1-methyl-1H-indol-3-yl)-, N-(2-methyl-1H-indol-3-yl)-, and N-(1,2-dimethyl-1H-1-indol-3-yl)-4-nitrobenzamides, compounds 8, 10, and 19a-c, respectively.Treatment of 1 with 2-methoxyfuran forms the 2-benzoxazolyl-2-propenoate 14.