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ChemComm
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COMMUNICATION
Journal Name
F.L. Hong, Y. B. Chen, S. H. Ye, G.Y. ZhDuO, XI:.10Q.1.0Z3h9u/D, 0XC.CL0u1,0R6.5SK.
Liu and, L. W. Ye, J. Am. Chem. Soc., 2020. 142, 7618-7626;
(d) Y. He, Y. Liu, Y. Liu, X. X. Kou, Q. Z. Li, J. H. Li, H. Z. Jiang, H.
J. Leng, C. Peng and J. L. Li, Adv. Synth. Catal., 2020, 362,
2052-2058.
In conclusion, we have developed a one-pot, two-component
approach for the facile synthesis of 1,3-disubstitued 1,2,4-triazoles
from readily accessible hydrazonoyl chlorides and commercially
available NMI. The procedure that was proved to be initiated by
nucleophilic substitution of hydrazonoyl chloride with NMI,
revealed the unique overall action of NMI as a masked hydrogen
cyanide. This unprecedented formal [3 + 2] cycloaddition followed
by two C-N bond cleavages provides direct access to structurally
diverse 1,3-disubstitued-1H-1,2,4-triazoles. Short reaction time,
mild conditions, excellent yields, and diverse functional group
tolerance may be regarded as advantages of this metal-free
protocol. The transformations proceeded without much sensitivity
to electronic or steric hindrance factors, and the targeted five-
membered heterocycles were obtained in 71-96% yields.
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We gratefully acknowledge the Research Council of Tarbiat
Modares University for support of this work.
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Conflicts of interest
There are no conflicts to declare.
Notes and references
1
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2
o NMI as a masked HCN
o Two C-N bond cleavages
o Excellent yields
HC
N
3
4
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o Short reaction time
o Practical purification
o Metal & catalyst free procedure
H
Cl
NHN
N
H
N
R
17 examples
71-96% yields
N
R
N
N
Ph
MeCN, 70 oC, 4 h Ph
R = Alkyl, Aryl,
Heteroaryl
5
6
7
8
9
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11, 1296-1298; (b) K. Müller-Buschbaum and Y. Mokaddem,
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Zubieta, Chem. Commun., 1998, 18, 2005-2006.
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2020, 22, 3239-3244; (b) M. J. Bird, S. M. Wales, C.
4 | J. Name., 2012, 00, 1-3
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