Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 2402-95-1, is researched, SMILESS is ClC1=CC=CC=[N+]1[O-], Molecular C5H4ClNOJournal, European Journal of Organic Chemistry called Stabilized 2,3-pyridyne reactive intermediates of exceptional dienophilicity, Author is Connon, Stephen J.; Hegarty, Anthony F., the main research direction is regioselective lithiation thiophenoxy chloropyridine; thiophenoxy pyridyne preparation; pyridine endoxide preparation.Name: 2-Chloropyridine 1-oxide.
The enhanced dienophilicity of 4-methoxy, 4-aryloxy and 4-thiophenoxy analogs of 2,3-pyridyne relative to itself is reported. The regioselective lithiation of 4-alkoxy- and 4-thiophenoxy-2-chloropyridine at low temperatures, followed by elimination of lithium chloride affords 4-alkoxy- and 4-thiophenoxypyridynes, which can be trapped in situ in a [4+2] cycloaddition reaction with furan to give endoxides in moderate to good yields (25-58%). In contrast, precursors with a hydrogen or Me substituent at C-4 give no evidence for pyridyne formation under these conditions. Attempts to generate 6-isopropoxy-2,3-pyridyne from the low-temperature lithiation of 2-chloro-6-isopropoxypyridine were unsuccessful due to the instability of the 2-chloro-6-isopropoxy-5-lithiopyridine.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem