4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles
Тип публикации: Journal Article
Дата публикации: 2015-07-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
A wide range of electron-poor 4-bromo-/4-chloro-2-azabuta-1,3-dienes were synthesized by the Rh2(OAc)4-catalyzed reaction of diazo esters and diazo ketones with methyl 2-halo-2H-azirine-2-carboxylates. The E stereoselectivity with respect to the configuration of the CC bond of the 2-azadiene moiety is in good agreement with the results of DFT (M06-2X/6-31+G(d,p)) calculations of the reaction pathway. The reaction proceeds via the formation of an azirinium ylide intermediate followed by ring opening with outward rotation of the halogen atom. Depending on the substitution pattern at C1 electron-poor 4-halo-2-azabutadienes can undergo two types of cyclization at elevated temperatures: reversible 1,4-electrocyclization to give 2,3-dihydroazetes or 1,5-exo-trig cyclization to give 5-methylene-2,5-dihydrooxazoles, both in good yields. The dihydrooxazole derivatives can be also obtained at ambient temperature under DBU catalysis.
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Smetanin I. A. et al. 4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles // Tetrahedron. 2015. Vol. 71. No. 28. pp. 4616-4628.
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Smetanin I. A., Novikov M. S., Rostovskii N. V., Khlebnikov A. F., Starova G. L., Yufit D. S. 4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles // Tetrahedron. 2015. Vol. 71. No. 28. pp. 4616-4628.
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TY - JOUR
DO - 10.1016/j.tet.2015.05.022
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402015006663
TI - 4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles
T2 - Tetrahedron
AU - Smetanin, Ilia A
AU - Novikov, Mikhail S.
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Starova, G. L.
AU - Yufit, Dmitry S.
PY - 2015
DA - 2015/07/01
PB - Elsevier
SP - 4616-4628
IS - 28
VL - 71
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2015_Smetanin,
author = {Ilia A Smetanin and Mikhail S. Novikov and Nikolai V Rostovskii and Alexander F Khlebnikov and G. L. Starova and Dmitry S. Yufit},
title = {4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles},
journal = {Tetrahedron},
year = {2015},
volume = {71},
publisher = {Elsevier},
month = {jul},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040402015006663},
number = {28},
pages = {4616--4628},
doi = {10.1016/j.tet.2015.05.022}
}
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Smetanin, Ilia A., et al. “4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles.” Tetrahedron, vol. 71, no. 28, Jul. 2015, pp. 4616-4628. https://linkinghub.elsevier.com/retrieve/pii/S0040402015006663.