metódy syntézy n- regioizomérnych arnhoxazolov
DESCRIPTION
Metódy syntézy N- regioizomérnych ArNHoxazolov. Mgr. Peter Šramel, Katedra organickej chémie, PriF UK. Glycerol. Narsaiah, A. V.; Ghogare, R. S.; Biradar, D. O. Org. Commun. 2011 , 75 – 81. Narsaiah, A. V.; Ghogare, R. S.; Biradar, D. O. Org. Commun. 2011 , 75 – 81. PEG 400. - PowerPoint PPT PresentationTRANSCRIPT
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NH
O
N
Metódy syntézy N- regioizomérnych ArNHoxazolov
Mgr. Peter Šramel, Katedra organickej chémie, PriF UK
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Glycerol
NH
NH2
O+
BrO
glycerol
RT, 1.5 h NH
O
N
90 %
1.00 mol ekv 1.00
Narsaiah, A. V.; Ghogare, R. S.; Biradar, D. O. Org. Commun. 2011, 75 – 81.
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Narsaiah, A. V.; Ghogare, R. S.; Biradar, D. O. Org. Commun. 2011, 75 – 81.
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PEG 400
NH
NH2
O+
BrO
PEG 400
RT, 3 h NH
O
N
79 %
1.00 mol ekv 1.00
Gokhale, K. M.; Wagal, O.; Kanitkar, A. Int. J. Pharm. Phytopharmacol. Res. 2012, 4, 156 – 160.
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Gokhale, K. M.; Wagal, O.; Kanitkar, A. Int. J. Pharm. Phytopharmacol. Res. 2012, 4, 156 – 160.
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DES (cholínchlorid : močovina – 1 : 1)
NH
NH2
O+
BrO
DES
RT, US, 17 min NH
O
N
86 %
1.00 mol ekv 1.00
Singh, B. S.; Lobo, H. R.; Pinjari, D. V.; Jarag, K. J.; Pandit, A. B.; Shankarling, G. S. Ultrason. Sonochem. 2013, 20, 287 – 293.
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Singh, B. S.; Lobo, H. R.; Pinjari, D. V.; Jarag, K. J.; Pandit, A. B.; Shankarling, G. S. Ultrason. Sonochem. 2013, 20, 287 – 293.
![Page 9: Metódy syntézy N- regioizomérnych ArNHoxazolov](https://reader036.vdocuments.pub/reader036/viewer/2022081422/568166e9550346895ddb2ba7/html5/thumbnails/9.jpg)
Singh, B. S.; Lobo, H. R.; Pinjari, D. V.; Jarag, K. J.; Pandit, A. B.; Shankarling, G. S. Ultrason. Sonochem. 2013, 20, 287 – 293.
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Al2O3 (zásaditý)
NH
NH2
O+
BrO
Al2O3 (zásaditý)
CH2Cl2, MW (140 °C)120 s
NH
O
N
95 %
1.00 mol ekv 1.00
Cl
Cl
Kidwai, M.; Dave, B.; Bhushan, K. R. Chem. Papers 2000, 4, 231 – 234.
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Kidwai, M.; Dave, B.; Bhushan, K. R. Chem. Papers 2000, 4, 231 – 234.
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Kidwai, M.; Dave, B.; Bhushan, K. R. Chem. Papers 2000, 4, 231 – 234.
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Etanol (klasická metóda)
NH
NH2
O+
BrO
reflux, 8 h NH
O
N
55 %
1.00 mol ekv 1.00
F
Cl
Cl EtOH
Pathak, V. N.; Goyal, M. K.; Meenakshi, J.; Krishna, C. J. J . Indian. Chem. Soc. 1993, 70, 539 – 542.
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Etanol + 1M HCl
NH
NH2
O+
BrO
reflux, 30 h NH
H2N O
N
? %
1.00 mol ekv 1.00
EtOH, 1M HClH2N
Haviv, F.; Ratajczyk, J. D.; DeNet, R. W.; Kerdesky, F. A.; Walters, R. L. et al. J. Med. Chem. 1988, 31, 1719 – 1728.
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DMF
H2N NH2
O+
BrO
reflux H2N O
N
30 - 37 %
1.00 mol ekv 1.00
DMF
O
HN R
O
HN
O
RO
Snangguan, S.; Wang, F.; Liao, Y.; Yu, H.; Li, J.; Huang, W.; Hu, H.; Yu, L.; Hu, Y.; Sheng, R. Molecules 2013, 18, 3577 – 3594.
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DMF
N NH2
O+
BrO
100 °C, 24 h
N O
N
20 - 60 %
1.00 mol ekv 1.00
DMF
CF3S
R1
R2
SF3C
R2
R1
Wang, G. T.; Wang, S.; Gentles, R.; Sowin, T.; Leitza, S.; Reilly, E. B.; von Geldern, T. W. Bioorg. Med. Chem. Lett. 2005, 15, 195 – 201.
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Wang, G. T.; Wang, S.; Gentles, R.; Sowin, T.; Leitza, S.; Reilly, E. B.; von Geldern, T. W. Bioorg. Med. Chem. Lett. 2005, 15, 195 – 201.
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AN
H2N NH2
O+
reflux, 12 h H2N O
N
70 %
1.00 mol ekv 10.00
ANBrO
Cl
Cl
Cl Cl
Patent; President and Fellows of Harvard College; Chorev, M.; Aktas, B. H.; Halperin, J. A.; Wagner, G.; WO2012/6068 2012, (A2).
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DMF + EtOH
NH
NH2
O+
EtOH, reflux NH
O
N
82 %
1.00 mol ekv 1.00
DMFBr
O
OO
Dabholkar, V. V.; Pandey, R. V.; Patil, S. R. J. Heterocyclic Chem. 2013, 50, 403 – 407.
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Deoxo-F
Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165 – 1168.
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Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165 – 1168.