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n ‐Butyl by‐products in the syntheses of 2‐(1‐ and 2‐naphthyl)pyridines via lithiation
Author(s) -
Klemm L. H.,
Burel William,
Purtzer Daniel
Publication year - 1992
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.5570290654
Subject(s) - chemistry , pyridine , ether , butyllithium , medicinal chemistry , organic chemistry
By‐products in the syntheses of 2‐(1‐ and 2‐naphthyl)pyridines by successive treatments of 1‐ and 2‐bromonaphthalenes with (a) n ‐butyllithium in ether and (b) pyridine are identified as 5‐butyl‐2‐(1‐naphthyl)pyridine and, tentatively, 5‐butyl‐2‐(2‐naphthyl)pyridine, respectively. It is proposed that these by‐products result from reaction of intermediate compounds 1‐lithio‐2‐naphthyl‐1,2‐dihydropyridines and 1‐bromobutane.