Tetrakis(acetonitrile)copper(I) Hexafluorophosphate
Letters in Organic Chemistry, 2012, Vol. 9, No. 2
131
[
[
[
[
5]
6]
7]
8]
Bazgir, A.; Seyyedhamzeh, M.; Yasaei, Z.; Mirzaei, P. A novel
three-component method for the synthesis of triazolo[1,2-
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General Procedure for the Synthesis of Compounds 5
and 6
Bagley, C. M.; Davis, T.; Dix, M. C.; Rokicki, M. J.; Kipling, D.
Rapid synthesis of VX-745: p38 MAP kinase inhibition in Werner
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Aromatic aldehyde 1 (1.0 mmol), dimedone 2 (1.0
mmol), phthalhydrazide 3 (1.0 mmol), or 4-phenylurazole 4
(
3 4 6
1.0 mmol) and [Cu(CH CN) ]PF (15 mol %) are placed in
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a mortar. The reaction mixture was then heated at 100 °C for
an appropriate time (Table 1) until the completion of the
reaction was achieved as monitored by TLC. Then, the
reaction mixture was cooled, washed with acetone (15 mL)
and evaporated under vacuum to give the product, which was
crystallized from ethyl acetate/n-hexane (1:3) to afford pure
[9]
5
or 6.
,4-Dihydro-3,3-dimethyl-13-(4-chlorophenyl)-2H-inda-
zolo[2,1-b]phthalazine-1,6,11(13H)-trione (5b): White
powder (90%); mp 261-263 ꢀC. IR (KBr) (vmax, cm ):
[
10]
3
-
1
1
2
959, 1659, 1625. H NMR (300 MHz, CDCl
3
): ꢀ, ppm; 1.21
CO), 3.27 and 3.38 (2H, AB
2
), 6.42 (1H, s, CH), 7.20-8.36
[11]
(
6H, s, 2Me), 2.34 (2H, s, CH
2
system, 2JHH = 19.1 Hz, CH
(
8H, m, H-Ar).
[
12]
13]
6
,7-Dihydro-6,6-dimethyl-2-phenyl-9-(4-fluorophenyl)-
[
1,2,4]-triazolo[1,2-a]indazole-1,3,8(2H,5H,9H)- trione (6c):
White powder (89%); mp 103–105 ꢀC. IR (KBr) (vmax,
-
1
1
[
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cm ): 2958, 1785, 1723, 1662. H NMR (300 MHz, CDCl
, ppm; 1.21 (3H, s, Me), 1.22 (3H, s, Me), 2.35 (2H, s,
CH CO), 2.92-3.10 (2H, AB system, 2JHH = 19.5 Hz, CH ),
.19 (1H, s, CH), 7.43–7.57 (9H, m, H–Ar).
3
):
ꢀ
2
2
6
[14]
Heine, H. W.; Baclawski, M.; Bonser, S. M.; Wachob, G. D.
Diaziridines. 5. Reaction of some 1-aroyl- and 1,2-
diacyldiaziridines. J. Org. Chem. 1976, 41, 3229.
[
15]
16]
Liu, L. P.; Lu, J. M.; Shi, M. PhI(OAc)(2)-mediated novel 1,3-
dipolar cycloaddition of methylenecyclopropanes (MCPs),
vinylidenecyclopropanes (VCPs), and methylenecyclobutane
ACKNOWLEDGEMENT
We wish to thank the research council of Bu-Ali Sina
University, Hamedan, Iran, for financial support to carry out
this research.
(MCB) with phthalhydrazide. Org. Lett. 2007, 9, 1303.
[
(a) Bebernitz, G. R.; Argentieri, G.; Battle, B.; Brennan, C.;
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SUPPLEMENTARY MATERIAL
Supplementary material is available on the publishers
Web site along with the published article.
CONFLICT OF INTEREST
Declared none.
[
[
[
17]
18]
19]
Azarifar, D.; Nejat Yami, R. Ultrasonic-assisted one-pot synthesis
of Pyrazolo[1,2-a][1,2,4]triazole-1,3-diones. Heterocycles. 2010,
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