Dihydroisoquinoline rearrangement, XXXV: 6,7-Dihydro-7-(3,4-dimethoxybenzyl)-6-methylthieno[2,3-c]pyridine

Article abstract of DOI:10.1002/ardp.19833161104

The title compound 4 is synthesized from the 7-chlorotheinopyridine 1 via the 7-(dimethoxybenzyl) compound 2 which is obtained by Wittig alkylation. Compound 2 is methylated by methyl iodide to give the iminium salt 3 which is reduced with LiAlH₄ to yield 4. When 4 is treated with 0.1 N-HCl the disproportionation products 3 and 5 are formed. Moreover, the rearrangement product 6 is obtained in 6% yield. Compound 6 was isolated as the pseudocyanide 7.