100067-09-2Relevant academic research and scientific papers
One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition
Wang, Li-Ya,Tsai, Henry J.,Lin, Hui-Yi,Kaneko, Kimiyoshi,Cheng, Fen-Ying,Shih, Hsin-Siao,Wong, Fung Fuh,Huang, Jiann-Jyh
, p. 14215 - 14220 (2014/04/17)
A one-flask strategy for the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles 4a-s and 8a and b from nitriles 5a-i with N-arylhydrazonoyl hydrochlorides 3a-h and 7a and b under basic conditions was developed. The reaction provided the desired 1,2,4-triazoles in moderate to excellent yields (56-98%), and was applicable to aliphatic and aromatic nitriles as well as N-phenylhydrazonoyl hydrochlorides bearing ester and acetyl functionalities. A 1,3-dipolar cycloaddition between imidate and nitrilimine generated from the respective nitrile and N-arylhydrazonoyl chloride in one flask was proposed for the new transformation.
Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties
Wang, Li-Ya,Tseng, Wen-Che,Wu, Tian-Shung,Kaneko, Kimiyoshi,Takayama, Hiroyuki,Kimura, Masayuki,Yang, Wen-Chin,Wu, Jin Bin,Juang, Shin-Hun,Wong, Fung Fuh
supporting information; experimental part, p. 5358 - 5362 (2011/10/03)
An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoro- and trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt3 as catalytic basic agent to provide the corresponding product in 28-94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine- and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2,4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells.
'One-flask' synthesis to 3,5-disubstituted 1,2,4-triazoles from aldehydes with hydrazonoyl hydrochlorides via 1,3-dipolar cycloaddition
Tseng, Wen-Che,Wang, Li-Ya,Wu, Tian-Shung,Wong, Fung Fuh
, p. 5339 - 5345 (2011/07/31)
A new 'one-flask' synthesis of 3,5-disubstituted 1,2,4-triazoles has successfully been developed to synthesize a series of 3,5-disubstituted 1,2,4-triazoles. The transformation involves the 1,3-dipolar cycloaddition reaction of hydrazonoyl hydrochlorides with oxime intermediates prepared from aldehydes with hydroxylamine hydrochloride in the presence of excess amount of triethylamine. In this 'one-flask' 1,3-dipolar reaction, hydrazonoyl hydrochlorides was concerned as the masked 1,3-dipole nitrilimine under basic condition. Furthermore, this newly developed methodology can be applied to various aldehyde substrates including aliphatic, cyclic aliphatic, aromatic, and heterocyclic aldehydes. Crown Copyright
An effective nitrilimine cycloaddition for the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from oximes with hydrazonoyl hydrochlorides
Wang, Li-Ya,Tseng, Wen-Che,Lin, Hui-Yi,Wong, Fung Fuh
, p. 1467 - 1471 (2011/08/03)
An effective 1,3-dipolar cycloaddition for the synthesis of 1,3,5-trisubstituted 1,2,4-triazole derivatives was developed by reacting oximes with hydrazonoyl hydrochlorides using triethylamine as a base. The desired 1,3,5-trisubstituted 1,2,4-triazoles were obtained in good yields and the reaction was applicable to aliphatic, cyclic aliphatic, aromatic and heterocyclic oxime substrates. Georg Thieme Verlag Stuttgart - New York.
An Improved Synthesis of 1H-1,2,4-Triazoles from C-Triphenylphosphinimino-hydrazones
Bruche, Luca,Garanti, Luisa,Zecchi, Gaetano
, p. 772 - 774 (2007/10/02)
1-Phenyl-1H-1,2,4-triazoles 5a-h are prepared in good yields by reaction of the triphenylphosphine imide 1 with acyl chlorides 2a-h and subsequent base treatment of the intermediate phosphonium salts 3a-h.
Ketone Enamines as Dipolarophiles towards C-Azidohydrazones
Bruche, Luca,Garanti, Luisa,Zecchi, Gaetano
, p. 1903 - 1906 (2007/10/02)
The reaction of methyl azido(phenylhydrazono)acetate (1) with the enamines (4)-(7) leads to different kinds of ring-closed products, namely 1,2,4-triazines (8)-(10), 1,2,3-triazoles (12)-(15), and 1,2,4-triazoles (16)-(19).An open-chain azo compound (20) is also formed.In one case, an intermediate 4,5-dihydro-1H-1,2,3-triazole (11) has been isolated.A mechanistic picture is proposed involving preliminary cycloaddition of the azido group to the enamine and subsequent reaction of the 4,5-dihydro-1H-1,2,3-triazoles according to various concurrent pathways.
