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Furan ring recyclization in 2‐furfurylthieno[2,3‐ b ]pyridines: An intramolecular N‐alkylation of pyrrole ring under acid conditions
Author(s) -
Kosulina Darya Yu.,
Vasilin Vladimir K.,
Stroganova Tatyana A.,
Kaklyugina Tatyana Ya.,
Krapivin Gennady D.
Publication year - 2010
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.311
Subject(s) - chemistry , furan , ring (chemistry) , pyrrole , intramolecular force , alkylation , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The preparation of new 3‐amino‐2‐furfurylthieno[2,3‐ b ]pyridines ( 1a , 1b , 69–80%) is described. Subsequent acidic rearrangement of 1a , 1b afforded two new annulated heterocyclic products, 5a , 5b , pyrrolothieno[2,3‐ b ]pyridines (45–74%), and 6 , pyridothieno[2,3‐ b ]pyrrolizine (22%), depending on reaction conditions. J. Heterocyclic Chem., (2010).