ChemInform Abstract: Enolate-Mediated 1,3-Dipolar Cycloaddition Reaction of β-Functionalized Ketones with Nitrile Oxides: Direct Access to 3,4,5-Trisubstituted Isoxazoles.

ChemInform ◽  
2016 ◽  
Vol 47 (42) ◽  
Author(s):  
Xiao Zhou ◽  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Kun Liu ◽  
Hua Gao ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles

2016 ◽  
Vol 14 (23) ◽  
pp. 5246-5250 ◽  
Author(s):  
Xiao Zhou ◽  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Kun Liu ◽  
Hua Gao ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
High Yields

Enolate-mediated [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazole in high yields and regioselectivities.

Direct access to isoxazolino and isoxazolo benzazepines from 2-((hydroxyimino)methyl)benzoic acid via a post-Ugi heteroannulation

2017 ◽  
Vol 15 (27) ◽  
pp. 5737-5742 ◽  
Author(s):  
Saeed Balalaie ◽  
Mohammad Shamakli ◽  
Ali Nikbakht ◽  
Nahid S. Alavijeh ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

A diversity-oriented access to isoxazolino and isoxazolo benzazepines is elaborated via a post-Ugi heteroannulation involving intramolecular 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes and alkynes.

Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones

2010 ◽  
Vol 63 (3) ◽  
pp. 445 ◽  
Author(s):  
Nicola J. Beattie ◽  
Craig L. Francis ◽  
Andris J. Liepa ◽  
G. Paul Savage
Keyword(s):  
Cycloaddition Reaction ◽  
Biphasic System ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
Facial Selectivity

Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.

Direct access to 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of allyl ketones with azides

2014 ◽  
Vol 16 (6) ◽  
pp. 3003-3006 ◽  
Author(s):  
Wenjun Li ◽  
Zhiyun Du ◽  
Jiayao Huang ◽  
Qianfa Jia ◽  
Kun Zhang ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition

A general organocatalytic 1,3-dipolar cycloaddition reaction between allyl ketones and various azides is reported. The reaction is catalyzed by a secondary amine to generate substituted 1,2,3-triazoles with high levels of regioselectivity.

Study on the 1,3-dipolar cycloaddition reaction of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one with nitrile oxides

Tetrahedron ◽  
2007 ◽  
Vol 63 (10) ◽  
pp. 2315-2319 ◽  
Author(s):  
Huiling Jiang ◽  
Weimin Yue ◽  
Huihong Xiao ◽  
Shizheng Zhu
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

Lead tetraacetate oxidation of hindered alicyclic ketoximes

1970 ◽  
Vol 48 (6) ◽  
pp. 966-969 ◽  
Author(s):  
G. Just ◽  
K. Dahl
Keyword(s):  
Cycloaddition Reaction ◽  
Lead Tetraacetate ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

Lead tetraacetate oxidation of 2,2,6,6-tetramethylcyclohexanone oxime and structurally related ketoximes caused C—C bond fission to yield acetyl hydroxamates. Severely hindered ketoximes gave nitrile oxides as intermediates which were trapped by 1,3-dipolar cycloaddition reaction.

scholarly journals 1,3-Dipolar Cycloaddition Reaction of Substituted Trimethylstannylacetylenes with Nitrile Oxides.

1993 ◽  
Vol 41 (3) ◽  
pp. 478-480 ◽  
Author(s):  
Takao SAKAMOTO ◽  
Daishi UCHIYAMA ◽  
Yoshinori KONDO ◽  
Hiroshi YAMANAKA
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

scholarly journals Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides

ARKIVOC ◽  
2004 ◽  
Vol 2004 (4) ◽  
pp. 137-152 ◽  
Author(s):  
Benito Alcaide ◽  
Pedro Almendros ◽  
Elena Sáez
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides
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