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Diversely Substituted Imidazo[1,2‐ a ]pyrazine‐8‐oxo‐3‐carbaldehydes: An Iodine‐Mediated Cyclization/Oxidation Approach
Author(s) -
Mishra Nigam M.,
Vachhani Dipak D.,
Modha Sachin G.,
Van der Eycken Erik V.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201150
Subject(s) - chemistry , alkyne , amination , intramolecular force , combinatorial chemistry , pyrazine , iodine , catalysis , organic chemistry
A mild and efficient iodine‐mediated intramolecular heteroannulation approach for the construction of the imidazo[1,2‐ a ]pyrazinone core has been developed. Under ambient conditions, this metal‐free protocol allows easy access to densely functionalized imidazo[1,2‐ a ]pyrazinone‐3‐carbaldehydes or (aminomethyl)imidazo[1,2‐ a ]pyrazinones from substrates containing terminal alkynes by cyclization and subsequent oxidation or amination. Further diversification may be introduced by using substrates containing an internal alkyne and/or Suzuki coupling after cyclization to generate polysubstituted (dihydro)imidazo[1,2‐ a ]pyrazinones.