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Synthesis of nitrooxazoles
Author(s) -
Hammar W. James,
Rustad Mark A.
Publication year - 1981
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.5570180507
Subject(s) - chemistry , halogenation , substituent , bromine , yield (engineering) , iodine , nitro , sequence (biology) , halo , medicinal chemistry , organic chemistry , alkyl , biochemistry , materials science , physics , quantum mechanics , galaxy , metallurgy
A reaction sequence involving halogenation and replacement of the halo substituent by a nitro group using dinitrogen tetraoxide has led to a general, convenient route to 5‐nitrooxazoles. Reaction schemes employing both bromine and iodine as the halo substituent have been investigated; however, the method using iodine preceded by a mercuration step affords a better overall yield in the range of 20–50%. Both 2‐ and 4‐nitro‐oxazoles can be prepared by this latter sequence, though in lower overall yields (4–12%).