So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Sen, Chiranjit; Ghosh, Subhash C. researched the compound: 8-Hydroxyquinoline 1-oxide( cas:1127-45-3 ).Application of 1127-45-3.They published the article 《Transition-Metal-Free Regioselective Alkylation of Quinoline N-Oxides via Oxidative Alkyl Migration and C-C Bond Cleavage of tert-/sec-Alcohols》 about this compound( cas:1127-45-3 ) in Advanced Synthesis & Catalysis. Keywords: alkyl quinoline oxide regioselective preparation; quinoline oxide alc alkyl migration bond cleavage PIDA mediated; isoquinoline alkyl oxide regioselective preparation; alc isoquinoline oxide alkyl migration bond cleavage PIDA mediated; pyridine alkyl oxide regioselective preparation; oxide pyridine alc aalkyl migration bond cleavage PIDA mediated. We’ll tell you more about this compound (cas:1127-45-3).
An unprecedented C2-alkylation of quinoline N-oxide derivatives I [R1 = Me, Et; R2 = H, OH, HNC(O)Ph, etc.; R3 = H, 6-Me, 5-Br, etc.] via C-C bond activation of tert- and sec-alkyl alc. was described using hypervalent iodine (III) reagent PhI(OAc)2 (PIDA). This regioselective alkylation using mild hypervalent iodine reagents was more practical, operationally simple and transition metal-free. The reaction proceeded efficiently with a broad range of substrates including quinoline, isoquinoline, and pyridine N-oxides using a variety of tert-/sec- alcs. to afford compounds I, alkyl-benzo[h]quinoline-N-oxides, alkyl-pyridine-N-oxides and alkyl-isoquinoline-N-oxides. From exptl. outcome, a rationalized mechanism was proposed, mediated by PIDA.
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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider