57772-50-6Relevant academic research and scientific papers
Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling
Tatevosyan, Stepan S.,Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Lukashev, Nikolay V.,Beletskaya, Irina P.
supporting information, p. 369 - 377 (2021/10/21)
A convenient approach to assemble 1,2,3-triazole-fused 4 H -3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C-O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C-I bond was achieved by the use of Na 2CO 3in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.
Pendant Alkoxy Groups on N-Aryl Substitutions Drive the Efficiency of Imidazolylidene Catalysts for Homoenolate Annulation from Enal and Aldehyde
Kyan, Ryuji,Mase, Nobuyuki,Narumi, Tetsuo,Sato, Kohei
supporting information, p. 19031 - 19036 (2020/08/25)
Hydrogen-transfer in the tetrahedral intermediate generated from an imidazolylidene catalyst and α,β-unsaturated aldehyde forms a conjugated Breslow intermediate. This is a critical step affecting the efficiency of the NHC-catalyzed γ-butyrolactone formation via homoenolate addition to aryl aldehydes. A novel type of imidazolylidene catalyst with pendant alkoxy groups on the ortho-N-aryl groups is described. Catalyst of this sort facilitates the formation of the conjugated Breslow intermediate. Studies of the rate constants for homoenolate annulation affording γ-butyrolactones, reveal that introduction of the oxygen atoms in the appropriate position of the N-aryl substituents can increase the efficiency of imidazolylidene catalysts. Structural and mechanistic studies revealed that pendant alkoxy groups can be located close to the proton of the tetrahedral intermediate, thereby facilitating the proton transfer.
Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives
Zhang, Jingjing,Xu, Wentao,Qu, Yi,Liu, Yuxiu,Li, Yongqiang,Song, Hongjian,Wang, Qingmin
supporting information, p. 15212 - 15215 (2020/12/21)
Herein, we report the first protocol for visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides. The protocol, which has good functional group tolerance and a broad substrate scope, constitutes an efficient and general route to difluoromethylated spiro[indole-3,3′-quinoline] derivatives. This journal is
Adenosine receptor antagonists
-
Paragraph 0309-0311, (2020/12/15)
The invention provides a compound shown as a formula (I) and a pharmaceutical composition thereof. The compounds of formula (I) of the present invention are useful as adenosine receptor inhibitors, especially A2A and/or A2B inhibitors, for example, the product can be used for prevention or treatment of diseases associated with A2A and/or A2B activity or expression.
Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation
Liu, Youran,Chen, Fei,He, Yan-Mei,Li, Chenghao,Fan, Qing-Hua
, p. 5099 - 5105 (2019/05/29)
A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.
Catalytic Asymmetric [4 + 3] Annulation of C, N-Cyclic Azomethine Imines with Copper Allenylidenes
Wang, Yanfang,Zhu, Liping,Wang, Mengran,Xiong, Jiale,Chen, Nannan,Feng, Xing,Xu, Zhaoqing,Jiang, Xianxing
supporting information, p. 6506 - 6510 (2018/10/20)
The first asymmetric decarboxylative [4 + 3] annulation of propargylic carbamates with C,N-cyclic azomethine imines has been developed successfully by a copper-N-heterocyclic carbine system. This strategy led to a series of optically active isoquinoline-f
PhI(OAc)2-mediated dearomative C-N coupling: Facile construction of the spiro[indoline-3,2′-pyrrolidine] skeleton
Zhou, Yali,Li, Dengke,Tang, Shi,Sun, Hongwei,Huang, Jinbo,Zhu, Qiang
supporting information, p. 2039 - 2042 (2018/03/27)
A facile construction of the spiro[indole-3,2′-pyrrolidine] skeleton, through diacetoxyiodobenzene (PIDA) mediated C-N bond-forming dearomatization of C3 sulfonamide linked indole derivatives, has been developed. A variety of spiro-indolepyrrolidines were
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
supporting information, 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.
Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives
Hao, Jiping,Xu, Yi,Xu, Zhongliang,Zhang, Zhiqiang,Yang, Weibo
supporting information, p. 7888 - 7892 (2019/01/04)
A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N-H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative coupling annulation of allylic sulfones without using peroxides or any metal oxidants. This developed protocol affords 7-membered ring heterocyclic compounds incorporating both sulfone-containing amino acid esters and one quaternary carbon center. Mechanistic studies indicate that an unusual umpolung of glycine occurred in this annulation.
Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles
Cao, Bo,Simaan, Marwan,Marek, Ilan,Wei, Yin,Shi, Min
supporting information, p. 216 - 219 (2016/12/27)
A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.
