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Alexander Tuan-Huy Duong Bryan J. Simmons Mohammad Parvez Alam Jesus Campagna Neil K. Garg Varghese John 《Tetrahedron letters》2019,60(3):322-326
This study describes our development of a microfluidic reaction scheme for the synthesis of fused indoline ring systems found in several bioactive compounds. We have utilized a continuous-flow microfluidic reactor for the reaction of hydrazines with latent aldehydes through the interrupted Fischer indolization reaction to form fused indoline and azaindoline products. We have identified optimal conditions and evaluated the scope of this microfluidic reaction using various hydrazine and latent aldehyde surrogates. This green chemistry approach can be of general utility to rapidly produce indoline scaffolds and intermediates in a continuous manner. 相似文献
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Here, the synthesis of two novel series of dichromophoric cyanine dyes were reported. The first series of novel bis-azacyanine dyes 3a–d was afforded by reaction of 2-(1,3,3-trimethyle indoline-2-ylidene)acetaldehyde with diaminoaromatics, and the second series of novel bis-diazacyanine dyes 4a–d was obtained using quaternization of an amine group in disazo compounds, which were produced by the reaction of disazoaromatics with 2-methylene-1,3,3-trimethyle indoline. The products were identified by 1H NMR, 13C NMR, infrared, UV-vis, and mass spectroscopy. 相似文献
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seco-Iso-cyclopropylfurano[e]indoline-trimethoxyindole 1 and seco-cyclopropylfurano[f]quinoline-trimethoxyindole 2 are potent cytotoxic agents. Previous synthesis of these compounds was inefficient and the approach required separation of a mixture containing the isomeric indoline and quinoline intermediates 11 and 12, formed from radical cyclization of allylic bromide 10. Reported herein is an efficient and selective synthesis of either intermediate 11 or 12, thus product 1 or 2, as needed. The conditions of the Stobbe condensation, bromination, 5-exo-trig radical cyclization, amine-carboxylic acid coupling, and debenzylation were optimized for multi gram scale. As a result, the reaction times were shortened, the products were readily isolated, and the yields and purity improved. 相似文献
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Hajime Yokoyama Takayoshi KuboYosuke Matsumura Junichi HosokawaMasahiro Miyazawa Yoshiro Hirai 《Tetrahedron》2014
The synthesis of indole skeleton by using Pd(II)-catalyzed cyclization of the urethane has been achieved. The urethanes with allylic alcohol were converted into vinyl indolines in good yield. The vinyl indoline was transformed into some intermediates of indole alkaloids. 相似文献
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Ir(III)‐Catalyzed C7‐Position‐Selective Oxidative CH Alkenylation of Indolines with Alkenes in Air 下载免费PDF全文
An efficient method for C7‐position‐selective alkenylation of N‐substituted indolines with alkenes is reported. Various 7‐alkenylindolines were obtained in moderate to excellent yields in air in the presence of catalytic amounts of [Cp*IrCl2]2, AgOTf, and Cu(OAc)2. The protocol relies on the use of a carbonyl or carbamoyl group on the nitrogen atom of indoline as a directing group and is potentially applicable to the synthesis of 7‐alkenylindoles and 7‐alkylindoles. 相似文献
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Functional organic dyes have promising prospect in dye-sensitized solar cells as a crucial element, of which sensitizers based on donor-π-acceptor are the most important dyes. On the basis of the structures of the aromatic amine donors such as triphenylamine and indoline, this paper reviews the photoelectric conversion properties of organic sensitizers since 2008, and highlights research work in our laboratory in this area. 相似文献
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B. S. Lukyanov A. N. Utenyshev V. V. Tkachev S. M. Aldoshin V. I. Minkin M. B. Lukyanova Yu. S. Alekseenko 《Chemistry of Heterocyclic Compounds》2008,44(2):163-169
The structure of an indoline spiropyran of molecular formula C29H33NO2 has been studied by X-ray crystallographic analysis. Structural parameters have been determined for this spiropyran, containing
a condensed furan fragment with a tert-butyl group, in comparison with the structure of other spiropyrans of this series.
The observation in the absorption spectrum of a photoinduced cis-cis isomer is linked with its stabilization by the steric
effect of the bulky tert-butyl group and the strength of barriers at 77 K.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 221–228, February, 2008. 相似文献
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Palladium(0)‐Catalyzed Intermolecular Allylic Dearomatization of Indoles by a Formal [4+2] Cycloaddition Reaction 下载免费PDF全文
Run‐Duo Gao Qing‐Long Xu Bo Zhang Yiting Gu Prof. Li‐Xin Dai Prof. Dr. Shu‐Li You 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(33):11601-11604
Bridged indoline derivatives were synthesized by an intermolecular Pd‐catalyzed allylic dearomatization reaction of substituted indoles. The reaction between indoles and allyl carbonates bearing a nucleophilic alcohol side‐chain proceeds in a cascade fashion, providing bridged indolines in excellent enantioselectivity. 相似文献
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