Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles
M I Pleshchev
1
,
V Yu Petukhova
1
,
V. V. Kuznetsov
1
,
D V Khakimov
1
,
T. S. Pivina
1
,
Yu V Nelyubina
2
,
N N Makhova
1
Тип публикации: Journal Article
Дата публикации: 2013-04-01
scimago Q3
БС2
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Краткое описание
A new metathesis reaction of azomethine imines is found. Catalytic or thermal diaziridine ring opening of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes leads to azomethine imines reacting further with het(aryl)methylidenemalononitriles to give in situ new azomethine imines inaccessible by common synthetic methods. New azomethine imines are detected as pyrazolines formed via a 1,4-H shift and trapped by the [3+2] cycloaddition with various dipolarophiles to yield 1,5-diazabicyclo[3.3.0]octane derivatives bearing pharmacophoric heterocycles, e.g. furan, nitrofuran, thiophene, and indole. The best results are achieved in the Et2O·BF3-catalyzed reactions in ionic liquids.
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Pleshchev M. I. et al. Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles // Russian Chemical Bulletin. 2013. Vol. 62. No. 4. pp. 1066-1075.
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Pleshchev M. I., Petukhova V. Yu., Kuznetsov V. V., Khakimov D. V., Pivina T. S., Nelyubina Yu. V., Makhova N. N. Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles // Russian Chemical Bulletin. 2013. Vol. 62. No. 4. pp. 1066-1075.
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TY - JOUR
DO - 10.1007/s11172-013-0143-9
UR - https://doi.org/10.1007/s11172-013-0143-9
TI - Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles
T2 - Russian Chemical Bulletin
AU - Pleshchev, M I
AU - Petukhova, V Yu
AU - Kuznetsov, V. V.
AU - Khakimov, D V
AU - Pivina, T. S.
AU - Nelyubina, Yu V
AU - Makhova, N N
PY - 2013
DA - 2013/04/01
PB - Springer Nature
SP - 1066-1075
IS - 4
VL - 62
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2013_Pleshchev,
author = {M I Pleshchev and V Yu Petukhova and V. V. Kuznetsov and D V Khakimov and T. S. Pivina and Yu V Nelyubina and N N Makhova},
title = {Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles},
journal = {Russian Chemical Bulletin},
year = {2013},
volume = {62},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s11172-013-0143-9},
number = {4},
pages = {1066--1075},
doi = {10.1007/s11172-013-0143-9}
}
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MLA
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Pleshchev, M. I., et al. “Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles.” Russian Chemical Bulletin, vol. 62, no. 4, Apr. 2013, pp. 1066-1075. https://doi.org/10.1007/s11172-013-0143-9.
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