A variety of neutral ruthenium−carbene complexes
RuCl2(carbene)(arene) 1 (carbene
=
C(NR)C6H4(NR), R
= Me (a), Et (b); arene =
p-Me-C6H4-iPr
(1), C6H3Me3
(2), C6Me6
(3))
have been prepared by reaction of
[RuCl2(arene)]2 precursors with the
enetetraamines
(RN)C6H4(RN)CC(NR)C6H4(NR)
I (R = Me) and II (R = Et).
RuC(NCH2Ph)CH2CH2(NCH2Ph)Cl2(p-cymene)
(4) was prepared similarly, whereas the reaction of
[RuCl2(cycloocta-1,5-diene)]
n
with I led to
the formation of the 16-electron neutral complex
RuCl2[C(NMe)C6H4(NMe)]3
(6). One of them (3a) was transformed into
the dihydride
derivative
RuH2(C(NMe)C6H4NMe)(C6Me6)
(5). The cyclic voltammograms of
derivatives
1−3 show that they are oxidized in the range
E1/2 = 1.03−1.31 V vs SCE and are more
electrophilic than the isoelectronic
RuCl2(PR3)(arene) complexes.
Derivatives 1a, 3a, and
3b act as efficient catalyst precursors for the
electrophilic activation of the C⋮C bond of
(Z)-3-methylpent-2-en-4-yn-1-ol to afford 2,3-dimethylfuran
in good yield via intramolecular
cyclization.
A number of novel benzimidazolium salts having aryl substituents such as N-phenyl, 4-chlorophenyl and various alkyl substituents were synthesized. Their microwave-assisted catalytic activities were evaluated in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions using a catalytic system consisting of Pd(OAc) 2 /K 2 CO 3 in DMF/H 2 O under mild reaction conditions with consistent high yields, except those of 2-bromopyridine.
A mixture of benzimidazole salts (2-7), Pd(OAc) 2 and K 2 CO 3 in DMF-H 2 O catalyzes the Suzuki-Miyaura cross-coupling reactions promoted by microwave irradiation resulting in high yield within a short time. In particular, the yield of the Suzuki-Miyaura reactions with aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (2-7) were identified by 1 H-13 C, NMR, IR spectroscopic methods and microanalysis. The molecular structure of 1 was determined by X-ray crystallography. The antibacterial and antifungal activities of the novel benzimidazole derivatives (1-7) were also tested against standard strains.
Amino acid and peptide conjugates of quinine were synthesized using microwave irradiation in 52-95% yields using benzotriazole methodology. The majority of these conjugates retain in vitro antimalarial activity with IC50 values below 100 nm, similar to quinine.
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