PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
5
SO NHNH
Completely Cured by One 6 mg/kg Oral Dose of a New
McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Synthesis
cr020109k; (c) McConville, M.; Fern ꢀa ndez, J.; Angulo-Barturen,
2
2
O
S
O
-
H O, H , N
S
2
2
2
+
2
a
MW
or
6
b
2a
O
S
OH
ꢀ
I.; Bahamontes-Rosa, N.; Ballell-Pages, L.; Casta n~ eda, P.; de
1
1
O
S
O
C oꢀ zar, C.; Crespo, B.; Guijarro, L.; Jim ꢀe nez-D ꢀı az, M. B.;
S
ꢀ
Mart ꢀı nez-Mart ꢀı nez, M. S.; de Mercado, J.; Santos-Villarejo, A.;
H
Sanz, L. M.; Frigerio, M.; Washbourn, G.; Ward, S. A.; Nixon,
G. L.; Biagini, G. A.; Berry, N. G.; Blackman, M. J.; Calder oꢀ n,
F.; O’Neill, P. M. Carbamoyl Triazoles, Known Serine Protease
5b00434. (d) Benny, B.-A.; Thomas, R.; Morten, J.; Garrick, S.;
Kristen, F.; Klaus Gjervig, J.; Huailing, Z.; Søren Møller, N.;
Sandra, H.; Arne, M.; Tine Bryan, S. Discovery of 1-[2-(2,4-
7
O
S
O
O
N
S
Ph
10
8
O
S
N
1a
S
H
S
Dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): A
Novel Multimodal Compound for the Treatment of Major
N
-H
N
Ph
Ph
S
N
S
N
3
a
9
Scheme 4. Proposed reaction mechanism.
the p-toluenesulfonyl hydrazide 2a was treated alone, the reac-
tion afforded 1,2-di-p-tolyldisulfane 6a and S-p-tolyl-4-meth-
ylbenzenesulfonothioate 6 b in 20% and 59% yields,
respectively (Equation (5)). On the basis of the above results
01300636. (g) Wilson, A. J.; Kerns, J. K.; Callahan, J. F.;
D.; Chatterjee, T.; Ranu, B. C. Magnetically Separable CuFe
2
2 4
O
[
7d,7g,20]
Nanoparticles Catalyzed Ligand-Free C-S Coupling in Water:
Access to (E)- and (Z)-Styrenyl-, Heteroaryl and Sterically
and previous reports,
a plausible mechanism of this
transformation was proposed and shown in Scheme 4. Initially,
treatment of sulfonyl hydrazides of 2a under the reaction con-
dition gives the sulfonothioate 6 b. Subsequently, a regioselec-
tive Friedel-Crafts reaction on C-3 position of 1a generates the
intermediate 9. Finally, deprotonation of intermediate 9 pro-
vides the product 3a. In this transformation, the intermediate 8
is converted to sulfinic acid 11 in the presence of water, which
can supply the active sulfonothioate 6 b in this reaction cycle.
M. C. Edler; G. La Regina; A. Coluccia; M. C. Barbera; D.
Barrow; R. I. Nicholson; G. Chiosis; A. Brancale; E. Hamel; M.
Artico; Silvestri, R. New Arylthioindoles: Potent Inhibitors of
Tubulin Polymerization. 2. Structure-Activity Relationships and
C.; Fusillo, V.; Pigeaux, M.; Rokicki, M. J.; Kipling, D.
Microwave-Assisted Ullmann C-S Bond Formation: Synthesis of
Conclusion
[
2] (a) Zhi, C.; Wang, Q.; Liu, S.; Xue, Y.; Shi, L.; Zhu, X.; Hao, X.-
Q.; Song, M.-P. Cu-Catalyzed Direct C7 Sulfonylation of
In conclusion, we have developed a simple and efficient
method for the sulfenylation of imidazo[2,1-b]thiazoles with
sulfonyl hydrazides under microwave-assisted and catalyst-
free conditions. This transformation exhibits a broad scope
of the reaction substrates and good functional-group toler-
ance. Ongoing research including expanding the substrate
scope and applications of MAOS technology in organic syn-
thesis are currently underway in our lab.
N. S-Aryl Arenesulfonothioate and Copper Acetate Mediated
Ravi, C.; Reddy, N. N. K.; Pappula, V.; Samanta, S.; Adimurthy,
S.
Copper-Catalyzed
Three-Component
System
for
(
d) Ding, Y.; Xie, P.; Zhu, W.; Xu, B.; Zhao, W.; Zhou, A. Cu-
catalyzed sulfenylation of imidazol[1,2-a]pyridine via C-H func-
Funding
The work was financially supported by the Foundation for Natural
Science Foundation of Guangdong Province (2017A030313297) and
special funds of key disciplines construction from Guangdong and
Zhongshan cooperating.
Tran, L. D.; Popov, I.; Daugulis, O. Copper-promoted sulfenyla-
2
Casola, K. K.; Oliveira, C. E. S.; Zeni, G. Copper Oxide
Nanoparticle-Catalyzed Chalcogenation of the Carbon-
Hydrogen
Bond
in
Thiazoles:
Synthesis
of
2-
2
References
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2 2 3