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Cu(I) substitutions. furo[3,2‐ b ] pyridines, furo[3,2‐ c ] pyridines and 1 h ‐thieno[3,4‐ b ] 2‐pyran‐l‐ones from cuprous acetylides
Author(s) -
Mladenović S. A.,
Castro C. E.
Publication year - 1968
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.5570050213
Subject(s) - chemistry , pyran , substituent , ring (chemistry) , nucleophile , aryl , stereochemistry , medicinal chemistry , organic chemistry , alkyl , catalysis
The reaction of cuprous acetylides with aryl halides bearing a nucleophilic ortho substituent provides a versatile route to heterocyclic substances. The present work portrays the ease with which polyheterosystems can be constructed with this reaction. The synthesis of 2‐substituted 7‐iodofuro[3,2‐ c ]pyridines, 2‐substituted furo[3,2‐ b ]pyridines, and 3‐substituted l H ‐thieno‐[3,4‐ b ]‐2‐pyran‐l‐ones (thiaisocoumarins) is described. The latter two ring systems have not been previously reported.