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Synthesis of 4‐methylfuro[3′,2′:5,6]benzofuro[3,2‐ c ]pyridine
Author(s) -
Moron Jacqueline,
Bisagni Emile
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230606
Subject(s) - chemistry , pyridine , furan , medicinal chemistry , stereochemistry , organic chemistry
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 ).