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

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Abstract
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(2H) one (7) and 8,9‐dihydro‐4‐methylfuro[3′,2′:5,6]benzofuro[3,2c]pyridin‐1(2H)‐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).