Synthesis of 4‐methylfuro[3′,2′:5,6]benzofuro[3,2‐ c ]pyridine

4‐Methylfuro[3′,2′:5,6]benzofuro[3,2‐ c ]pyridine ( 3 ) was synthetized from 2‐acetylfuro[3,2‐ f ]benzo[ b ]furan ( 4 ) or from 2‐acetyl‐5,6‐dihydrofuro[3,2‐ f ]benzo[ b ]furan ( 10 ). The key step involves a rearrangement‐cyclization of azides 6 and 12 to form 4‐methylfuro[3′,2′:5,6]benzofuro[3,2‐ c ]pyridin‐1(2 H ) one ( 7 ) and 8,9‐dihydro‐4‐methylfuro[3′,2′:5,6]benzofuro[3,2 c ]pyridin‐1(2 H )‐one ( 13 ). Introduction of an aminoalkyl chain on carbon 1 was effected by substitution of 1‐chloro‐4‐methylfuro[3′,2′:5,6]benzofuro[3,2‐ c ]pyridine ( 8 ).