Synthesis of phosphorus- containing fused heterocyclic systems based on 2-substituted-1- arylimidazoles Carried out by: Kirilchyuk Andrey Supervisor: Zarudnitskii Evgeniy, Institute of Organic Chemistry Kyiv – 2010 National Technical Institute of Ukraine “Kyiv Polytechnical Institute”
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Synthesis of phosphorus-containing fused heterocyclic systems based on 2-substituted-1-arylimidazoles
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Synthesis of phosphorus-containing fused
heterocyclic systems based on 2-substituted-1-arylimidazoles
Carried out by: Kirilchyuk Andrey
Supervisor: Zarudnitskii Evgeniy,
Institute of Organic Chemistry
Kyiv – 2010
National Technical Institute of Ukraine“Kyiv Polytechnical Institute”
Introduction
N
N
PR2
Me Me
Me
N
N
NH2
P(OEt)2
O
Rib
N
N
R P
CH(OMe)2
N
PO3H2
N
NH
O
CO2H
N
N
N
NRP
NHRO
R'
N
N
i-Pr P
Et3
R = i-Pr, t-Bu, Ph
R = Cy, Bu-t
RPR 119990
P
3
1
2
3
4 5 6
Harkal S., Beller M. et al. // Adv. Synth. Catal. 2004, 346, 1742.
Kunz P. C., Kläui W. //Collect. Czech. Chem. Commun., 2007, 72, 492
Jimonet P. et al. // Bioorg. Med. Chem. Lett. 2001, 11, 127.
Bartlett P. A., Hunt J. T. et al. // Bioorg. Chem. 1978, 7, 421.
Buchanan J. G., Wightman R. H. // J. Chem. Soc. Perkin. Trans. 1, 1990, 955.
Bell R.A.et al. // Inorg. Chim. Acta, 1998, 274, 137.
2
Introduction
Kunz P. C., Kläui W. // Eur. J.
Inorg. Chem. 2003, 21, 3945.
(EtO)2P
O
NC
NH2
N
NBr
MeS CO2Me
bn
N
N
R P
R'
N
ON
EtO2C
P(OEt)2
H
O
NH
NP(OEt)2
O
EtO2C N
NP(OEt)2
N
O
bz
N
N
PR''2
Ar
N
N
Alk .
PPh2
(EtO)3CH
BzNH2
(EtO)2P(O)H
(Ph3P)4Pd
3 n-BuLi, -78oCPCl3 or R''2PCl
+
+
7
8
9 10 11
12
13
14
15
Толмачев А. А., Юрченко А. А и др. // ЖОХ, 1993, 63, 714.
Lin J., Thompson Ch. M. // J. Heterocycl. Chem., 1994, 31, 1701.
Bartlett P. A., Hunt J. T. et al. // Bioorg. Chem. 1978, 7, 421.
Jimonet P. et al. // Bioorg. Med. Chem. Lett. 2001, 11, 127.
Nishikawa H. et al. // Polyhedron 2001, 20, 627
3
4,5-dihydrobenzo[е]imidazo[2,1-с]
[1,4,2]diazophosphinine
N
N
N
P
Ar
O
X
R
16
Ivanov, V. V. et al. Heteroat. Chem., 2002, 13, 84 – 92. Ivanov, V. V. et al. Chem. Heterocyc. Compd., 2002, 38, 349 – 353.
• 1,2-Disubstituted imidazoles react with phosphorus (III) halides in pyridine regioselectively at position 5. The reaction proceeds more readily, the higher the electron-donating ability of the 2-substituent in the starting imidazole.
• Interaction of tri-valent phosphorus halides with 1-(2-(4-R-amino)phenyl)-2-methylthio-imidazole in basic medium proceeds at amino-group and the 5th position of the imidazole ring affording a derivative of previously unknown heterocyclic system – benzo[e]imidazo[1,5-c][1,4,2]diazophosphinine.
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Published works
• Kyrylchuk A. Enhancement of the Classical Suzuki Coupling in Transactions of Annual Students Conference “Innovations in Science and Technology”, Kyiv, March 25, 2008.: Book of Abstracts
• Кирильчук А. А., Зарудницкий Е. В. Синтез катализаторов нового типа для реакции сочетания Сузуки в Збірці тез доповідей учасників І Міжнародної (ІІІ Всеукраїнської) конференції студентів, аспірантів та молодих вчених з хімії та хімічної технології, Київ, 23 – 25 квітня 2008 р.