Synthesis of Isoxazoline-fused Chlorins by 1,3-Dipolar Cycloaddition Reaction of Porphyrins with Alkyl Nitrile Oxides

Heterocycles ◽  
2006 ◽  
Vol 68 (5) ◽  
pp. 885 ◽  
Author(s):  
Stanislaw Ostrowski ◽  
Stanislaw Ostrowski ◽  
Przemyslaw Wyrebek ◽  
Agnieszka Mikus
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

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.

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

scholarly journals Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

2019 ◽  
Vol 15 ◽  
pp. 1434-1440
Author(s):  
Xiujun Liu ◽  
Xiang Ma ◽  
Yaqing Feng
Keyword(s):  
Crystal Structure ◽  
Carbonyl Group ◽  
Mass Spectra ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Steric Interaction ◽  
Dimeric Complex ◽  
Nitrile Oxides ◽  
H Nmr ◽  
Basic Features

Isoxazoline-linked porphyrins have been synthesized by a regioselective 1,3-dipolar cycloaddition reaction between vinylporphyrin 2 and nitrile oxides. The steric interaction directed the reaction trajectory, in which only the product with a link between the 5-position of the isoxazoline and the β-position of porphyrin was observed. The isoxazoline-porphyrins 3a,b have been characterized by absorption, emission, 1H NMR and mass spectra. Later, the crystal structure of 3a was obtained and confirmed the basic features of the NMR-derived structure. Furthermore, a pair of enantiomers of 3a presented in the crystal, which formed a dimeric complex through intermolecular coordination between the Zn2+ center and the carbonyl group of the second molecule.

Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides

2016 ◽  
Vol 52 (9) ◽  
pp. 743-749 ◽  
Author(s):  
Ilya V. Efimov ◽  
Yuri M. Shafran ◽  
Natalia N. Volkova ◽  
Nikolai A. Beliaev ◽  
Pavel A. Slepukhin ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

ChemInform Abstract: 1,3-Dipolar Cycloaddition Reaction of Substituted Trimethylstannylacetylenes with Nitrile Oxides.

ChemInform ◽  
2010 ◽  
Vol 25 (7) ◽  
pp. no-no
Author(s):  
T. SAKAMOTO ◽  
D. UCHIYAMA ◽  
Y. KONDO ◽  
H. YAMANAKA
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides
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