Syntheses of oxazolo[4,5‐ c ]pyridine and 6‐azaindole | Zendy

Tjosaas Freddy | Zendy; Kjerstad Ivar Broendbo | Zendy; Fiksdahl Anne | Zendy

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Syntheses of oxazolo[4,5‐ c ]pyridine and 6‐azaindole

Author(s) -

Tjosaas Freddy,

Kjerstad Ivar Broendbo,

Fiksdahl Anne

Publication year - 2008

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.5570450240

Subject(s) - chemistry , pyridine , sonogashira coupling , yield (engineering) , catalysis , base (topology) , medicinal chemistry , organic chemistry , combinatorial chemistry , palladium , mathematical analysis , materials science , mathematics , metallurgy

The preparation of oxazolo[4,5‐ c ]pyridine and 6‐azaindole from 4‐bromo‐3‐pivaloylaminopyridine ( 8 ) is reported. The oxazolopyridine 2‐ tert ‐butyl‐oxazolo[4,5‐ c ]pyridine ( 9 ) was successfully prepared from 8 in 78% yield by a new base/TBAB promoted non‐catalyzed microwave cyclisation strategy (10 min) or, alternatively, in 54% yield by conventional heating (48 hrs) and CuI catalysis. The 6‐azaindole 2‐phenyl‐1‐(trimethylacetyl)‐6‐azaindole ( 13 ) was prepared from 8 in a two step procedure, including a Sonogashira coupling reaction.

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