- Synthesis and structural characterization of arene d6 metal complexes of sulfonohydrazone and triazolo ligands: High potency of triazolo derivatives towards DNA binding
-
Complexation of [(p-cymene)RuCl2]2 and [Cp?MCl2]2 (M = Rh/Ir) with chelating ligand 4-methylbenzenesulfonohydrazone ligands (L1 and L3) resulted in the formation of mononuclear cationic complexes having PF6
- Shadap, Lathewdeipor,Joshi, Nidhi,Poluri, Krishna Mohan,Kollipara, Mohan Rao,Kaminsky, Werner
-
-
Read Online
- Transannulation of Pyridotriazoles with Naphthoquinones and Indoles: Synthesis of Benzo[f]Pyrido[1,2-a]Indoles and Indolizino[3,2-b]indoles
-
Ruthenium catalysed denitrogenative transannulation of pyridotriazoles with naphthoquinones provided the transannulated benzo[f]pyrido[1,2-a]indoles derivatives in good to excellent yields. While pyridotriazoles with indoles in presence of PivOH and oxone yield indolizino[3,2-b]indoles under metal-free conditions. Quinone annulation proceeds through ruthenium-carbenoid intermediate while indole annulation may proceed via a diazo-pyridinium intermediate. Control experiments suggest that both the transformations follow the ionic mechanism. (Figure presented.).
- Rawat, Deepa,Adimurthy, Subbarayappa
-
-
- Nitrous oxide as a diazo transfer reagent: The synthesis of triazolopyridines
-
Nitrous oxide is a potential diazo transfer reagent, but its applications in organic chemistry are scarce. Here, we show that triazolopyridines and triazoloquinolines are formed in the reactions of metallated 2-alkylpyridines or 2-alkylquinolines with N2O. The reactions can be performed under mild conditions and give synthetically interesting triazoles in moderate to good yields.
- Landman, Iris R.,Fadaei-Tirani, Farzaneh,Severin, Kay
-
p. 11537 - 11540
(2021/11/16)
-
- Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones
-
A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
- Huang, Xiang,Chen, Xing,Xie, Haisheng,Tan, Zheng,Jiang, Huanfeng,Zeng, Wei
-
supporting information
p. 6784 - 6788
(2021/09/08)
-
- Method for synthesizing [1,2,3]triazole[1,5-a]pyridines compound through non-catalyst N-N coupling reaction
-
The invention relates to a method for synthesizing [1,2,3]triazole[1,5-a]pyridines compound through non-catalyst N-N coupling reaction. The invention discloses an efficient method for synthesizing a product at one step without using a catalyst under a mild condition from a 2-pyridylamine compound and nitroso tert-butyl ester as a mild nitrogen atom source. The method is free from the catalyst, thereaction step is reduced, the condition is extremely mild, the efficiency is high, and the later modification can be performed on the biological active molecular, thereby facilitating the industrialproduction of [1,2,3]triazole[1,5-a]pyridines compound.
- -
-
Paragraph 0032-0037; 0048-0052; 0063-0065
(2019/04/04)
-
- Recyclable Heterogeneous Copper(II)-Catalyzed Oxidative Cyclization of 2-Pyridine Ketone Hydrazones towards [1,2,3]Triazolo[1,5-a]pyridines
-
The heterogeneous copper(II)-catalyzed oxidative cyclization of 2-pyridine ketone hydrazones was achieved in ethyl acetate at room temperature in the presence of an MCM-41-anchored bidentate 2-aminoethylamino copper(II) catalyst [MCM-41-2N-Cu(OAc) 2
- Cai, Mingzhong,Jiang, Gan,Lin, Yang,Zhao, Hong
-
p. 4487 - 4497
(2019/11/21)
-
- TBAB-Catalyzed Csp3–N Bond Formation by Coupling Pyridotriazoles with Anilines: A New Route to (2-Pyridyl)alkylamines
-
A new metal-free procedure allowing Csp3–N bond formation through coupling of pyridotriazoles and weakly nucleophilic anilines has been developed. This sustainable reaction shows high tolerance towards functional groups (ketones, free alcohols) leading to 2-picolylamine derivatives. The key to our success is the use of a catalytic amount of TBAB and water as a co-solvent leading to the formation of pyridylalkylamine derivatives. As this coupling tolerates the presence of Csp2–Br bond on both partners of the reaction, we performed a sequential one-pot reaction between functionalized triazolopyridines and anilines followed by a second coupling with N-tosylhydrazones leading to the formation of Csp3–N and Csp2–Csp2 bonds.
- Lamaa, Diana,Lin, Hsin-Ping,Bzeih, Tourin,Retailleau, Pascal,Alami, Mouad,Hamze, Abdallah
-
supporting information
p. 2602 - 2611
(2019/04/16)
-
- Indium-catalyzed denitrogenative transannulation of pyridotriazoles: Synthesis of pyrido[1,2- A[indoles
-
Pyrido[1,2-a]indoles are known for medicinally and pharmaceutically important compounds; however, the efficient synthetic routes are scarce in the literature. We report herein a convenient and efficient route to synthesize these molecules through indium-catalyzed transannulation of pyridotriazoles with arenes. A library of compounds have been synthesized employing the method developed with various substituted pyrido[1,2-a]indole derivatives in moderate to good yields. The density functional theory study using SMDDCB-M06/6-31++G(d,p)/LANL2DZ//B3LYP/6-31G(d)/LANL2DZ method suggests that the reactions proceed via indium-carbenoid complex.
- Rawat, Deepa,Ravi, Chitrakar,Joshi, Abhisek,Suresh, Eringathodi,Jana, Kalyanashis,Ganguly, Bishwajit,Adimurthy, Subbarayappa
-
supporting information
p. 2043 - 2047
(2019/03/26)
-
- Palladium-Catalyzed Divergent Arylation with Triazolopyridines: One-Pot Synthesis of 6-Aryl-2-α-styrylpyridines
-
We have developed a new strategy for palladium-catalyzed arylation reactions with triazolopyridines, wherein two different chemical transformations (C-3 vs. C-7) are observed by differentiating the substrates using different bases. The reactive palladium carbenoids were directly generated from triazolopyridines and underwent denitrogenative arylations with aryl bromides. Intriguingly, when potassium carbonate was replaced with potassium tert-butoxide, direct C-H arylation occurred at the most acidic position (C-7). Moreover, two different catalytic arylation events were successfully performed in a one-pot sequence, providing a convenient access to 6-aryl-2-α-styrylpyridines.
- Moon, Youngtaek,Kwon, Soonhyung,Kang, Dahye,Im, Honggu,Hong, Sungwoo
-
supporting information
p. 958 - 964
(2016/04/05)
-
- Facile one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridines by copper(II)-catalyzed oxidative N-N bond formation
-
An efficient and simple method for the synthesis of various [1,2,3]triazolo[1,5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative N-N bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative N-N bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study. In the same pot: [1,2,3]Triazolo[1,5-a] pyridines are synthesized from the corresponding 2-acylpyridines by a one-pot method, consisting of hydrazonation followed by oxidative cyclization through copper(II)-catalyzed N-N bond formation (see scheme).
- Hirayama, Tasuku,Ueda, Satoshi,Okada, Takahiro,Tsurue, Norihiko,Okuda, Kensuke,Nagasawa, Hideko
-
supporting information
p. 4156 - 4162
(2014/04/17)
-
- Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: A general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines
-
A general and efficient NH insertion reaction of rhodium pyridyl carbenes derived from pyridotriazoles was developed. Various NH-containing compounds, including amides, anilines, enamines, and aliphatic amines, smoothly underwent the NH insertion reaction to afford 2-picolylamine derivatives. The developed transformation was further utilized in a facile one-pot synthesis of imidazo[1,5-a]pyridines.
- Shi, Yi,Gulevich, Anton V.,Gevorgyan, Vladimir
-
supporting information
p. 14191 - 14195
(2015/01/09)
-
- Crystal structures and spectral properties of two polyoxometalate-based inorganic-organic compounds from silver-azine building blocks with bis-bidentate and tridentate ligands
-
Two polyoxometalate-based inorganic-organic hybrid compounds constructed from silver(I)-L species and saturated Keggin type polyoxoanion, [Ag 2L21]2(SiMo12O40)·1. 5DMF·0.5CH3OH H2O 1 and [{Ag4L22(DMF) 5}(SiMo12O40)] 2 (L1 = phenyl 2-pyridyl ketone azine, L2 = 3-phenyltriazolo[1,5-a]pyridine), have been synthesized and structurally characterized by IR, UV, elemental analysis, XRPD and complete single crystal structure analyses, where the ligands L 1 and L2 are bis-bidentate and tridentate azines synthesized with the same materials under different conditions. The structure of 1 exhibits a dinuclear double-helicate with [SiMo12O 40]4- anions as counter ions, where all of the Ag centers coordinate to bis-bidentate chelating ligands. Compound 2 displays a two-dimensional sheet formed by the Ag-organic infinite chains and the [SiMo12O40]4- alternately arranged in a rail-like fashion. The luminescent properties of 1 and 2 in the solid state were investigated. 2014 Elsevier B.V.
- An, Bing,Zhou, Rui-Min,Sun, Li,Bai, Yan,Dang, Dong-Bin
-
p. 319 - 326
(2014/04/17)
-
- Ni-catalyzed alkenylation of triazolopyridines: Synthesis of 2,6-disubstituted pyridines
-
A synthetic strategy to access 2,6-disubstituted pyridines from triazolopyridines through a regioselective nickel-catalyzed alkenylation reaction of the C7-H bond is described. The N2 fragment embedded in the resulting C-H functionalized triazolopyridine can be readily excised using acidic or oxidative conditions to unmask the pyridine.
- Liu, Sheng,Sawicki, James,Driver, Tom G.
-
supporting information; experimental part
p. 3744 - 3747
(2012/08/28)
-
- Synthesis of novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines by Suzuki cross-coupling reactions
-
Two series of compounds, 3-aryl- (series A, compounds 2a-j) and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines (series B, compounds 3a-j) have been synthesized by Suzuki cross-coupling reactions, with a triazolopyridine halide and an aryl or heteroaryl b
- Abarca, Belén,Aucejo, Ricardo,Ballesteros, Rafael,Blanco, Fernando,García-Espa?a, Enrique
-
p. 8101 - 8103
(2007/10/03)
-
- Triazolopyridines. Part 24: New polynitrogenated potential helicating ligands
-
The synthesis of novel 7-{[1,2,3]triazolo[1,5-a]pyridin-3-yl}-[1,2,3] triazolo[1,5-a]pyridines 7, 2-pyridyl-[1,2,3]triazolo[1,5-a]pyrid-7-ylmethanols 11, 3-(6-substituted-2-pyridyl)-[1,2,3]triazolo[1,5-a]pyridines 12, and 7,7′-disubstituted-3,3′-[1,2,3]triazolo[1,5-a]pyridine 20, interesting polynitrogenated ligands as potential helicating compounds or luminescent sensors, from [1,2,3]triazolo[1,5-a]pyridines is described.
- Abarca, Belén,Ballesteros, Rafael,Chadlaoui, Mimoun
-
p. 5785 - 5792
(2007/10/03)
-
- Hypervalent iodine oxidation of hydrazones of some nitrogen heterocyclic ketones and aldehydes: An efficient synthesis of fused 1,2,3- triazoloheterocycles
-
Fused 1,2,3-triazoloheterocycles have been prepared by iodobenzene diacetate mediated oxidation of hydrazones of nitrogen heterocyclic ketones and aldehydes.
- Prakash, Om,Gujral, Harpreet K.,Rani, Neena,Singh, Shiv P.
-
p. 417 - 425
(2007/10/03)
-
- Control of the Stereochemistry of Kinetic Protonation: Intramolecular Proton Delivery
-
Four decades ago, we noted that for delocalized carbanions and enols the protonation transition state is close to sp2 hybridized and that, as a consequence, under kinetic control protonation takes place from the less hindered approach, most often with formation of the less stable of two possible stereoisomers. The initial report was followed by an extensive series of examples. Nevertheless, a major question remained, namely whether it was possible to deliver the proton to the more hindered face of such a species using intramolecular proton transfer. To this end, silyl ether precursors to the enols of 3-benzoyl-endo-6-phenyl-exo-6-pyridylbicyclo[3.1.0]hexane and its endo-6-pyridyl-exo-6-phenyl stereoisomer were synthesized. The corresponding enols were generated with fluoride anion. The endo-phenyl enol stereoisomers, on kinetic protonation, led stereoselectively to the endo-3-benzoyl product resulting from the less hindered protonation. In stark contrast, the endo-6-pyridyl enol isomer led stereoselectively to the exo-3-benzoyl ketone by intramolecular proton delivery. However, the kinetic orders of the stereochemistries differ; the intramolecular process requires additional proton donor molecules. The log of the ratio of the two stereochemistries is linear with the log of the proton donor concentration with the slope giving the difference in kinetic orders. An aromatic cyclic 14 electron Hueckel transition state is proposed. Additionally, the roles of acyl, nitro and cyano delocalizing groups were analyzed with ab initio computations.
- Zimmerman, Howard E.,Ignatchenko, Alexey
-
p. 6635 - 6645
(2007/10/03)
-
- Aerial oxidation of some 2-pyridyl ketone hydrazones catalyzed by Cu2+. Physical properties of reaction products
-
Some 2-pyridyl ketone hydrazones were subjected to aerial oxidation catalyzed by Cu2+. The oxidation product of di-2-pyridyl ketone hydrazone had the structure of a derivative of [1,2,3]-triazolo[1,5-a]pyridine, and this structure is different from that previously proposed by other investigators. The fluorescence spectra of the oxidation products were measured in solutions of a wide pH range. In contrast to the oxidation products of other 2-pyridyl ketone hydrazones, that of di-2-pyridyl ketone hydrazone showed very strong fluorescence in acidic media. The characteristic nature of this compound was also apparent in the ultraviolet spectrum. The generation of hydroxyl radical was demonstrated in the aerial oxidation of di-2-pyridyl ketone hydrazone catalyzed by Cu2+, suggesting the formation of hydrogen peroxide as another oxidation product.
- Mori,Sakamoto,Mashito,Matsuoka,Matsubayashi,Sakai
-
p. 1944 - 1947
(2007/10/02)
-