Chemistry of thienopyridines. IV. Syntheses of 5‐substituted thieno[2,3‐ b ] pyridines | Zendy

Klemm L. H. | Zendy; Zell Reinhard | Zendy

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Chemistry of thienopyridines. IV. Syntheses of 5‐substituted thieno[2,3‐ b ] pyridines

Author(s) -

Klemm L. H.,

Zell Reinhard

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.5570050606

Subject(s) - chemistry , pyridine , acylation , amide , ammonia , medicinal chemistry , base (topology) , liquid ammonia , chemical shift , potassium , schiff base , organic chemistry , stereochemistry , catalysis , mathematical analysis , mathematics

Chemical transformations on 5‐acetylthieno[2,3–6] pyridine produced 5‐NH 2 , 5‐CO 2 H, and 5‐CH 2 CO 2 H substituents. The 5‐amino compound underwent facile diazotization (plus Sand‐meyer reaction), Schiff's base formation, and acylation. Treatment of the derived 5‐bromo compound with potassium amide in liquid ammonia gave a mixture of 4‐amino (major) and 5‐amino isomers. Nmr spectral data are reported for the 5‐substituted thieno [2,3‐ b ] pyridine system.

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