3
11. Nielsen, F. E.; Bodvarsdottir, T. B.; Worsaae, A.; MacKay, P.;
Scheme 4. The reaction of TsNCO with urea, ethyleneurea and 1-
methyl-imidazolidin-2-one
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1141.
The proposed mechanism for formation of sulfonylguanidine
from urine is elucidated in Scheme 5. TsNCO is firstly
introduced to urine 1a to form a four-membered lactone 9a, and
then CO2 is released from the lactone to give the corresponding
sulfonylguanidine 2a. The X-ray structure of ketimine 2a is
shown in Figure 1.
O
O
NTs
N
CO2
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O
N
NTs
N
Ts
N C O
N
N
N
Radiopharm. 2018, 61, 773-779.
2a
1a
9a
18. Kamal, A.; Ahmed, S. K.; Reddy, K. S.; Khan, M. N. A.; Shetty, R. V.
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Scheme 5. The proposed mechanism for the reaction.
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Solvolysis of sulfonylguanidine 2a, which was conducted in
CF3COOH with methanesulfonic acid and thioanisole,34 formed
guandine 10a with 70% yield (Scheme 6).
NTs
NH
MeSO3H, PhSMe
CF3COOH
N
N
N
N
2a
10a
Scheme 6. Solvolysis of sulfonylguanidine 2a to corresponding
guanidine 10a.
22. Boverie, S.; Antoine, M.-H.; Somers, F.; Becker, B.; Sebille, S.;
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Conclusions
In summary, we have developed a simple way to synthesize
sulfonylguanidines from tetra-substituted urines with good
yields, which provides a convenient method for synthesis of
sulfonyl group protected guanidine in one step.
Acknowledgments
26. Shainyan, B. A.; Tolstikova, L. L.; Schilde, U. J. Fluorine Chem. 2012,
135, 261-264.
27. Tolstikova, L. L.; Chipanina, N. N.; Oznobikhina, L. P.; Shainyan, B.
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Zhizhko, Pavel A.; Gagieva, Svetlana Ch.; Zarubin, Dmitry N.;
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The authors gratefully acknowledge the Science and
Technology Project of Guizhou Province (QKHJC [2017]1027),
the Science and Technology Project of Guizhou Province
(QKHPTRC[2017]5788), “Chun Hui” Project of the Chinese
Ministry of Education (Z2017007), the talent introduction
Program of Guizhou University (GDRJHZ2014-21), and the
National Natural Science Foundation of China (No. 21901053).
31. Huang, D.; Dayun H.; Xuesong W.; Xingyong W.; Wenwen C.
; Xinyan W.;Yuefei H. Org. Lett. 2016, 18, 604-607.
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