Journal
TETRAHEDRON
Volume 67, Issue 47, Pages 9063-9066Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.08.090
Keywords
Electron density surface maps; Electrophilic aromatic substitution; Imidazopyrazine; Imidazopyridine
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Small heteroaromatic rings are valuable monomers in drug discovery that can enable rapid access to novel and desirable chemical space. Installation of a synthetic handle on a heteroaromatic core may be difficult if steric and electronic factors are not in alignment with the desired transformation. Described are practical routes for the construction of 5-bromo-6-methyl imidazopyrazine (1) as well as 5-bromo and 5-chloro-6-methyl imidazopyridines (2a and 2b), which were developed using electron density surface maps encoded with ionization potential to guide synthetic strategy. (C) 2011 Elsevier Ltd. All rights reserved.
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