Reactions of vinyl azides with .alpha.-oxo phosphorus ylides. Synthesis of N1-vinyltriazoles

Tandem Michael addition and Witting or Horner–Wadsworth–Emmons olefination initiated [3+3] annulation between vinyl azides and allylic phosphorus ylides or allylic phosphoryl-stabilized carbanions has been developed.

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ChemInform Abstract: [3 + 3] Annulation of Allylic Phosphoryl-Stabilized Carbanions/Phosphorus Ylides and Vinyl Azides: A Practice Strategy for Synthesis of Polyfunctionalized Anilines.

ChemInform ◽

10.1002/chin.201501076 ◽

2015 ◽

Vol 46 (1) ◽

Author(s):

Shen Liu ◽

Wenteng Chen ◽

Jing Luo ◽

Yongping Yu

Keyword(s):

Phosphorus Ylides ◽

Vinyl Azides

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Copper-catalyzed [2+3]-annulation of N–H imines with vinyl azides: access to polyaryl 2H-imidazoles

Chemical Communications ◽

10.1039/c9cc10042c ◽

2020 ◽

Vol 56 (42) ◽

pp. 5621-5624

Author(s):

Zhongzhi Zhu ◽

Hanze Lin ◽

Baihui Liang ◽

Junjie Huang ◽

Wanyi Liang ◽

...

Keyword(s):

Vinyl Azides ◽

By Products

A copper-catalyzed [2+3] annulation of N–H imines with vinyl azides to generate polyaryl 2H-imidazoles with N2 and H2O as the only by-products has been developed.

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Synthesis of Phenanthridine and Quinoxaline Derivatives via Copper‐Catalyzed Radical Cyanoalkylation of Cyclobutanone Oxime Esters and Vinyl Azides

Chinese Journal of Chemistry ◽

10.1002/cjoc.202100050 ◽

2021 ◽

Author(s):

Qi Liang ◽

Long Lin ◽

Guodong Li ◽

Xianqiang Kong ◽

Bo Xu

Keyword(s):

Quinoxaline Derivatives ◽

Vinyl Azides

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Visible-Light-Mediated Tandem Sulfonylation/Cyclization of Vinyl Azides with Sulfonyl Hydrazines for the Synthesis of 6-(Sulfonylmethyl)phenanthridines under Mild Conditions

Synlett ◽

10.1055/s-0037-1611758 ◽

2019 ◽

Vol 30 (08) ◽

pp. 955-960 ◽

Cited By ~ 10

Author(s):

Liu-Liang Mao ◽

Li-Xia Quan ◽

Xian-Hong Zhu ◽

Cong-Bin Ji ◽

An-Xi Zhou ◽

...

Keyword(s):

Visible Light ◽

Mild Conditions ◽

Simple Strategy ◽

Vinyl Azides

A visible-light-mediated tandem sulfonylation/cyclization of vinyl azides with sulfonyl hydrazines was developed that provides an efficient and simple strategy for the synthesis of valuable 6-(sulfonylmethyl)phenanthridines with a broad substrate scope and satisfactory yields under mild conditions.

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Copper-Catalyzed Aldol Reaction of Vinyl Azides with Trifluoromethyl Ketones

Organic Letters ◽

10.1021/acs.orglett.9b02616 ◽

2019 ◽

Vol 21 (18) ◽

pp. 7324-7328 ◽

Cited By ~ 6

Author(s):

Zhenhua Liu ◽

Zhihai Zhang ◽

Guangyu Zhu ◽

Yiqin Zhou ◽

Lin Yang ◽

...

Keyword(s):

Aldol Reaction ◽

Trifluoromethyl Ketones ◽

Vinyl Azides

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Chemistry of Phosphorus Ylides. Part 27. Metal Complexes of 4-hydroxyquinaldine, its Mannich Base and Phosphonium Ylide

Journal of Chemical Research ◽

10.3184/030823409x440841 ◽

2009 ◽

Vol 2009 (5) ◽

pp. 277-282 ◽

Cited By ~ 5

Author(s):

Fouad Soliman ◽

Ibrahim Abd-Ellah ◽

Soher Maigali ◽

Gamal Abd-El-Naim

Keyword(s):

Nitrogen Atom ◽

Metal Complexes ◽

Mannich Base ◽

Phosphorus Ylides ◽

Physicochemical Data

The reaction of Hg2+,Cd2+,Co2+, and Ni2+ ions with 1 mol of the ligands 2-methylquinoline-4-ol,3[(diethylamino)methyl]-2-methylquinoline-4-ol, and methyl-3-(4-hyrdoxy-2-methylquinoline-3-yl)-2-(triphenylphosphoranylidene)propanoate, has been investigated to give the corresponding 1:1 metal:ligand complexes. Reaction of 2 mol of the ligand gave the corresponding 1:2 metal:ligand complexes. The coordination takes place only through the quinoline nitrogen atom. The spectroscopic and the physicochemical data of the new metal complexes are discussed.

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