Synthesis, volume 53, issue 2, pages 348-358

An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage

Publication typeJournal Article
Publication date2020-09-29
Journal: Synthesis
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor2.6
ISSN00397881, 1437210X
Catalysis
Organic Chemistry
Abstract

A high-yielding method for the synthesis of 2H-1,3,5-oxadiazines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadiazoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.

Citations by journals

1
ACS Omega
ACS Omega, 1, 12.5%
ACS Omega
1 publication, 12.5%
Russian Journal of Organic Chemistry
Russian Journal of Organic Chemistry, 1, 12.5%
Russian Journal of Organic Chemistry
1 publication, 12.5%
Russian Journal of General Chemistry
Russian Journal of General Chemistry, 1, 12.5%
Russian Journal of General Chemistry
1 publication, 12.5%
Molecules
Molecules, 1, 12.5%
Molecules
1 publication, 12.5%
Organics
Organics, 1, 12.5%
Organics
1 publication, 12.5%
International Journal of Molecular Sciences
International Journal of Molecular Sciences, 1, 12.5%
International Journal of Molecular Sciences
1 publication, 12.5%
Organic Letters
Organic Letters, 1, 12.5%
Organic Letters
1 publication, 12.5%
Communications Chemistry
Communications Chemistry, 1, 12.5%
Communications Chemistry
1 publication, 12.5%
1

Citations by publishers

1
2
3
Multidisciplinary Digital Publishing Institute (MDPI)
Multidisciplinary Digital Publishing Institute (MDPI), 3, 37.5%
Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 37.5%
American Chemical Society (ACS)
American Chemical Society (ACS), 2, 25%
American Chemical Society (ACS)
2 publications, 25%
Pleiades Publishing
Pleiades Publishing, 2, 25%
Pleiades Publishing
2 publications, 25%
Springer Nature
Springer Nature, 1, 12.5%
Springer Nature
1 publication, 12.5%
1
2
3
  • 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.
Metrics
Share
Cite this
GOST |
Cite this
GOST Copy
Novikov M. S., Rostovskii N. V., Khlebnikov A. F. An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage // Synthesis. 2020. Vol. 53. No. 2. pp. 348-358.
GOST all authors (up to 50) Copy
Novikov M. S., Rostovskii N. V., Khlebnikov A. F. An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage // Synthesis. 2020. Vol. 53. No. 2. pp. 348-358.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/s-0040-1707278
UR - https://doi.org/10.1055%2Fs-0040-1707278
TI - An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage
T2 - Synthesis
AU - Novikov, Mikhail S.
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
PY - 2020
DA - 2020/09/29 00:00:00
PB - Thieme
SP - 348-358
IS - 2
VL - 53
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex Copy
@article{2020_Novikov
author = {Mikhail S. Novikov and Nikolai V Rostovskii and Alexander F Khlebnikov},
title = {An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage},
journal = {Synthesis},
year = {2020},
volume = {53},
publisher = {Thieme},
month = {sep},
url = {https://doi.org/10.1055%2Fs-0040-1707278},
number = {2},
pages = {348--358},
doi = {10.1055/s-0040-1707278}
}
MLA
Cite this
MLA Copy
Novikov, Mikhail S., et al. “An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage.” Synthesis, vol. 53, no. 2, Sep. 2020, pp. 348-358. https://doi.org/10.1055%2Fs-0040-1707278.
Found error?