Tetrahedron, volume 88, pages 132153
Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products
Publication type: Journal Article
Publication date: 2021-05-01
Journal:
Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract Methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates were synthesized and the product selectivity of their thermal Buchner reaction with benzene, naphthalene and mesitylene was studied. The reaction of the isoxazolyl-substituted diazoacetates with benzene gave a mixture of cycloheptatriene/norcaradiene isomeric adducts, which are in a rapid equilibrium. Heating the same diazo compounds with naphthalene led exclusively to stable norcaradiene adducts. In contrast, their thermal reaction with mesitylene gave only the products of carbene insertion into C-H bond of mesitylene. According to DFT calculations, such a difference in the product selectivity of the thermal Buchner reaction of the diazoacetates with benzene, naphthalene and mesitylene is associated with the fact that the first two reactions proceed under kinetic control, and the last one under thermodynamic control. Isoxazoles synthesized were converted to a new family of functionalized enaminones, (Z)-methyl 5-amino-2,5-diaryl-3-oxo-2-phenylpent-4-enoates, by reaction with Mo(CO)6/H2O hydrogenative reagent, wherein Mo(CO)6 catalyzes also the retro-Buchner reactions of the norcaradiene moiety of the starting compounds. The obtained enaminones are convenient precursors of 3,6-diaryl-4-hydroxy-3-phenylpyridin-2(1H)-ones, which were prepared from them under thermal conditions in high yields.
Citations by journals
|
1
|
|
|
Russian Journal of Organic Chemistry
|
Russian Journal of Organic Chemistry
1 publication, 16.67%
|
|
Beilstein Journal of Organic Chemistry
|
Beilstein Journal of Organic Chemistry
1 publication, 16.67%
|
|
RSC Advances
|
RSC Advances
1 publication, 16.67%
|
|
Chemical Papers
|
Chemical Papers
1 publication, 16.67%
|
|
Chemical Communications
|
Chemical Communications
1 publication, 16.67%
|
|
Russian Journal of General Chemistry
|
Russian Journal of General Chemistry
1 publication, 16.67%
|
|
1
|
Citations by publishers
|
1
2
|
|
|
Pleiades Publishing
|
Pleiades Publishing
2 publications, 33.33%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
2 publications, 33.33%
|
|
Beilstein-Institut
|
Beilstein-Institut
1 publication, 16.67%
|
|
Springer Nature
|
Springer Nature
1 publication, 16.67%
|
|
1
2
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2022,2023],"ids":[0,0],"codes":[0,0],"imageUrls":["",""],"datasets":[{"label":"Citations number","data":[4,2],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":["66.67","33.33"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Russian Journal of Organic Chemistry","Beilstein Journal of Organic Chemistry","RSC Advances","Chemical Papers","Chemical Communications","Russian Journal of General Chemistry"],"ids":[5728,21928,3100,4048,9073,13581],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp"],"datasets":[{"label":"","data":[1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[16.67,16.67,16.67,16.67,16.67,16.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Pleiades Publishing","Royal Society of Chemistry (RSC)","Beilstein-Institut","Springer Nature"],"ids":[101,123,6139,8],"codes":[0,0,0,0],"imageUrls":["\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp"],"datasets":[{"label":"","data":[2,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,33.33,16.67,16.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex
Cite this
GOST
Copy
Serebryannikova A. V. et al. Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products // Tetrahedron. 2021. Vol. 88. p. 132153.
GOST all authors (up to 50)
Copy
Serebryannikova A. V., Galenko E. E., Novikov M. S., Khlebnikov A. F. Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products // Tetrahedron. 2021. Vol. 88. p. 132153.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.tet.2021.132153
UR - https://doi.org/10.1016%2Fj.tet.2021.132153
TI - Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products
T2 - Tetrahedron
AU - Serebryannikova, Anna V
AU - Galenko, Ekaterina E
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2021
DA - 2021/05/01 00:00:00
PB - Elsevier
SP - 132153
VL - 88
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex
Copy
@article{2021_Serebryannikova,
author = {Anna V Serebryannikova and Ekaterina E Galenko and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products},
journal = {Tetrahedron},
year = {2021},
volume = {88},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016%2Fj.tet.2021.132153},
pages = {132153},
doi = {10.1016/j.tet.2021.132153}
}