Reaction of Aromatic N-Oxides with Dipolarophiles. I. Reaction Products of 3-Picoline 1-Oxide with Phenyl Isocyanate

Hisano, Takuzo; Yoshikawa, S.; Muraoka, Keiji

doi:10.1248/cpb.22.1611

Cited by 14 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of N-oxides of azines with phenyl isocyanate has been investigated since the early 1960s ( [97][98][99], and references therein). In its course, cycloaddition of N-oxide to the C¼N double bond leads to the formation of cycloadducts, which quickly undergo a 1,5-sigmatropic rearrangement to 2,3-dihydroazine intermediates, which in some cases can be isolated [100][101][102].…”

Section: Cycloaddition To Carbon-nitrogen Multiple Bondsmentioning

confidence: 99%

Recent Advances in Cycloaddition Reactions of Heterocyclic N-Oxides

Loska

2017

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

1,3-Dipolar cycloaddition of N-oxides of azines and azoles has become a reliable and versatile synthetic method of preparation of highly functionalized nitrogen heterocycles. Mechanisms of cycloaddition of N-oxides are outlined, including various reaction pathways available for the initial five-membered cycloadducts. Cycloaddition to multiple carbon-carbon, carbon-nitrogen, and carbon-sulfur bonds is discussed, with particular emphasis on modern methods of selective C-2-functionalization of the heteroaromatic ring.

show abstract

Section: Cycloaddition To Carbon-nitrogen Multiple Bondsmentioning

confidence: 99%

Recent Advances in Cycloaddition Reactions of Heterocyclic N-Oxides

Loska

2017

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

show abstract

“…6 Pyridine N -oxides activated with a phosphonium coupling reagent were shown to react with amines to give 2-aminopyridines by a Reissert− Henze-type reaction. 7 Reissert−Henze-type reactions were also employed in the synthesis of N -unsubstituted 8 and N -triflyl 2-aminopyridines.…”

mentioning

confidence: 99%

2-Aminopyridines via Reaction of Pyridine N-Oxides and Activated Isocyanides

Vamos

Cosford

2014

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…A number of rearrangements starting with N-oxides may be used as convenient methods for the introduction of substituents into aza-aromatic systems [1][2][3][4].…”

mentioning

confidence: 99%

“…Following the methodology for cyanation of 2-unsubstituted 1H-imidazole 3-oxides [11], the solutions of benzo[c][1,5]naphthyridine 5-oxide (2) and benzo[h][1,6]naphthyridine 6-oxide (3) in dry CH 2 Cl 2 in the presence of Et 3 N were treated with Me 3 SiCN. The temperature of the mixture was kept at 0-5°C, and the progress of the reaction was followed by TLC.…”

mentioning

confidence: 99%