68535-49-9Relevant academic research and scientific papers
Cycloaddition Reactions of in situ Generated C2D2 in Dioxane: Efficient Synthetic Approach to D2-Labeled Nitrogen Heterocycles
Voronin, Vladimir V.,Ledovskaya, Maria S.,Rodygin, Konstantin S.,Ananikov, Valentine P.
, p. 5640 - 5648 (2021/11/11)
In this work, an universal synthetic approach for the synthesis of D2-labeled nitrogen heterocycles based on cycloaddition reactions of in situ generated dideuteroacetylene is reported. A key feature of this method is the use of 1,4-dioxane as
[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles
Bi, Xihe,Ning, Yongquan,Sivaguru, Paramasivam,Wang, Hongwei,Zanoni, Giuseppe
supporting information, (2021/09/30)
1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.
The Hofmann reaction involving annulation of: O -(pyridin-2-yl)aryl amides selectively and rapidly leads to potential photocatalytically active 6 H -pyrido[1,2- c] quinazolin-6-one derivatives
Gao, Wenjing,Liu, Tongxin,Wan, Yameng,Wu, Hao,Zhang, Guisheng,Zhang, Zhiguo
supporting information, p. 7955 - 7961 (2020/11/30)
A highly efficient PIFA-mediated Hofmann reaction of o-(pyridin-2-yl)aryl amides has been developed to selectively and rapidly construct various potential photocatalytically active 6H-pyrido[1,2-c]quinazolin-6-one derivatives. The use of a nontoxic and ec
Microwave-assisted one-pot quick synthesis of 1-monosubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and 3-butyn-2-ols
Du, Zhonglin,Li, Fenrui,Li, Li,Li, Ran
, (2020/11/13)
Abstract: Microwave-assisted one-pot quick synthesis to 1-monosubstituted 1,2,3-triazoles was achieved with good to excellent yields using the widely available arylboronic acids, sodium azide and 3-butyn-2-ols within 15 min. This method features high effi
Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides
Giel, Marie-Claire,Smedley, Christopher J.,Mackie, Emily R. R.,Guo, Taijie,Dong, Jiajia,Soares da Costa, Tatiana P.,Moses, John E.
supporting information, p. 1181 - 1186 (2019/12/11)
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.
An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles
Patterson, Sarah J.M.,Clark, Peter R.,Williams, Glynn D.,Tomkinson, Nicholas C.O.
supporting information, (2020/10/13)
This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excellent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines.
Metal-free Semiconductor Photocatalysis for sp2 C?H Functionalization with Molecular Oxygen
Zheng, Meifang,Ghosh, Indrajit,K?nig, Burkhard,Wang, Xinchen
, p. 703 - 706 (2019/01/04)
Designing metal-free catalysts for solar energy conversion is a long-standing challenge in semiconductor photoredox catalysis (SPC). With visible-light-responsive hexagonal boron carbon nitride (h-BCN) as a non-metal photocatalyst, this system affords C?H/N?H coupling products with broad substitution tolerance and high efficiency with molecular oxygen as the terminal oxidant. The catalyst exhibits remarkable performance for the selective C?H functionalization of electron-rich arenes to C?N products (yields up to 95 %) and good stability (6 recycles). Both nitrogen heteroarenes and amine salts are competent coupling nucleophiles. Mechanically, the reactive oxygen species are superoxide anion radical (O2?.) and H2O2, which are proved by electron spin resonance (ESR) data, KI-starch, and control experiments. In addition, kinetic isotope effect (KIE) experiments indicate that C?H bond cleavage is not involved in the rate limiting step. This semiconductor-based photoredox system allows for C?H amination free of any metals, ligands, strong oxidants, and additives. It provides a complementary avenue to C?H functionalizations and enables synthetic applications efficiently in a sustainable manner.
Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling
Zhao, Yiming,Van Nguyen, Huy,Male, Louise,Craven, Philip,Buckley, Benjamin R.,Fossey, John S.
supporting information, p. 4224 - 4241 (2018/10/25)
Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. Bulky substrates wer
One-Pot Synthesis of 1-Monosubstituted 1,2,3-Triazoles from Propargyl Alcohol
Han, Chunmei,Dong, Suping,Zhang, Wensheng,Chen, Zhen
, p. 673 - 677 (2018/03/10)
A one-pot synthesis of 1-monosubstituted-1,2,3-triazoles from propargyl alcohol and various aryl azides was achieved. This simple method provides concise and efficient access to various 1-monosubstituted 1,2,3-triazole derivatives through a three-step one
One-pot synthesis of 1-monosubstituted-1, 2, 3-triazoles from 2-methyl-3-butyn-2-ol
Liu, Yaowen,Han, Chunmei,Ma, Xinyuan,Yang, Jianhua,Feng, Xuepu,Jiang, Yubo
supporting information, p. 650 - 653 (2018/01/15)
An efficient method for the synthesis of 1-monosubstituted-1, 2, 3-triazoles from 2-methyl-3-butyn-2-ol under copper catalyst conditions has been developed through a one-step one-pot sequence. This method provides a concise and efficient pathway to synthesize 1-monosubstituted-1, 2, 3-triazole derivatives in good to excellent yields.
