Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides
Publication type: Journal Article
Publication date: 2001-01-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Heating of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of N-arylmaleimides gives rise to 2,9-diarylperhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-diones. It is presumed that thermal cleavage of the C-N bond in the diaziridine fragment of the 6-aryl-1,5-diazabicyclo[3.1.0]hexanes results in formation of labile azomethinimines that react with N-arylmaleimides to afford the products of 1,3-dipolar cycloaddition. The rate of accumulation thereof depends only on the character of substituents in the aromatic ring of the 1,5-diazabicyclo[3.1.0]hexanes and is independent of maleimide. The thermal isomerization of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes without 1,3-dipolarophiles yields the corresponding 2-pyrazolines.
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Molchanov A. et al. Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides // Russian Journal of Organic Chemistry. 2001. Vol. 37. No. 6. pp. 841-851.
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Molchanov A., Sipkin D. I., Koptelov Yu. B., Kostikov R. R. Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides // Russian Journal of Organic Chemistry. 2001. Vol. 37. No. 6. pp. 841-851.
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TY - JOUR
DO - 10.1023/A:1012465732305
UR - http://link.springer.com/10.1023/A:1012465732305
TI - Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides
T2 - Russian Journal of Organic Chemistry
AU - Molchanov, A.P.
AU - Sipkin, D I
AU - Koptelov, Yu B
AU - Kostikov, R R
PY - 2001
DA - 2001/01/01
PB - Springer Nature
SP - 841-851
IS - 6
VL - 37
SN - 1070-4280
SN - 1608-3393
ER -
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BibTex (up to 50 authors)
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@article{2001_Molchanov,
author = {A.P. Molchanov and D I Sipkin and Yu B Koptelov and R R Kostikov},
title = {Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides},
journal = {Russian Journal of Organic Chemistry},
year = {2001},
volume = {37},
publisher = {Springer Nature},
month = {jan},
url = {http://link.springer.com/10.1023/A:1012465732305},
number = {6},
pages = {841--851},
doi = {10.1023/A:1012465732305}
}
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MLA
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Molchanov, A.P., et al. “Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides.” Russian Journal of Organic Chemistry, vol. 37, no. 6, Jan. 2001, pp. 841-851. http://link.springer.com/10.1023/A:1012465732305.