41626-19-1Relevant articles and documents
Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs
Jia, Tingting,Liu, Shourong,Shao, Jiaan,Shi, Tao,Wu, Zhaoxiao,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian,Zhuang, Rangxiao
, p. 8460 - 8463 (2021/09/08)
A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is
Palladium-Catalyzed cascade carbonylative synthesis of 1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN3
Du, Shiying,Wang, Wei-Feng,Song, Yufei,Chen, Zhengkai,Wu, Xiao-Feng
supporting information, p. 974 - 978 (2021/02/01)
A palladium-catalyzed three-component carbonylative reaction for the synthesis of 3H-1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN3 has been achieved. The reaction presumably proceeds through a cascade carbonylation, acyl azide format
[3+2]-cycloaddition of in situ generated nitrile imines and acetylene for assembling of 1,3-disubstituted pyrazoles with quantitative deuterium labeling
Voronin, Vladimir V.,Ledovskaya, Maria S.,Gordeev, Evgeniy G.,Rodygin, Konstantin S.,Ananikov, Valentine P.
, p. 3819 - 3828 (2018/04/14)
A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.
A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines
Guo, Zhenyan,Jia, Hao,Liu, Honglei,Wang, Qijun,Huang, Jiaxing,Guo, Hongchao
, p. 2939 - 2943 (2018/05/28)
An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.
Asymmetric catalytic 1,3-dipolar cycloaddition reaction of nitrile imines for the synthesis of chiral spiro-pyrazoline-oxindoles
Wang, Gang,Liu, Xiaohua,Huang, Tianyu,Kuang, Yulong,Lin, Lili,Feng, Xiaoming
supporting information, p. 76 - 79 (2013/04/10)
A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)2 complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.
The Preparation and Spectroscopic Properties of Some Di- and Tri-substituted 1,3,5-Triphenyl-2-pyrazolines and Related 2-Pyrazolines
Rivett, Donald E.,Rosevear, Judi,Wilshire, John F. K.
, p. 1649 - 1658 (2007/10/02)
The effect of substituents on the absorption and fluorescence properties of a number of di- and tri-para-substituted 1,3,5-triphenyl-2-pyrazolines, several substituted 1,3,5,5-tetraphenyl-and trans-1,3,4,5-tetraphenyl-2-pyranolines, and some 1,3-diphenyl-
Synthesis and reactions of 1H-4,1,2-benzothiadiazines, and observations on the structure of hydrazonoyl sulphides
Vukov, Darko J.,Gibson, Martin S.,Lee, William E.,Richardson, Mary F.
, p. 192 - 196 (2007/10/05)
Syntheses of 1-acetyl-7- and -8-bromo- and -6,8-dibromo-3-phenyl-4,1,2-benzothiadiazines establish, in conjunction with previous data, the generality of 1H-4,1,2-benzothiadiazine synthesis from appropriately substituted N′-acetyl-N′-arylbenzothiohydrazides. The corresponding 6-nitrobenzothiadiazine is also available by this route, and such cyclizations can proceed by expulsion of a nitro-group, presumably as nitrite ion. These 1H-4,1,2-benzothiadiazines undergo electrophilic substitution at positions 6 and 8, are nucleophilic at position 1, and are oxidizable at position 4 to the corresponding sulphone. X-Ray crystallographic studies of bis-[α-(2,6-dibromophenylhydrazono)benzyl] sulphide confirm the symmetrical structure of hydrazonoyl sulphides.
