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Several new heterocyclic systems based on a hydroxybenzofuro[2,3- b ]pyridine building block were prepared. This benzofuropyridine is easily available from the Meerwein reaction of benzoquinone and a heterocyclic diazonium salt, followed by reduction and cyclization. Electrophilic substitution and further condensations give polycyclic systems, including oxazolo- and chromeno-fused analogues., (Copyright © 2021, Singh et al.)