Sorption Properties of Phosphorylated Indoles

Sorption properties of 1- and 3-substituted indoles containing a P(III) atom were estimated by gas chromatography. The sorption properties were shown to depend on the nature of substituents on the phosphorus atom.     

Synthesis of Phosphorylated Nitrovinylindoles

Russian Journal of General Chemistry -     

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6‐difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well‐defined indole heterocycles.     

Efficient Synthesis of 2-Ethoxycarbonyl Indoles

An efficient one-pot procedure for the synthesis of 2-ethoxycarbonyl indoles from commercially available materials has been developed. The one-step procedure involves in situ formation of the hydrazones from phenylhydrazine hydrochloride and ethyl pyruvate in the presence of bismuth nitrate followed by Fischer cyclization in polyphosphoric acid and ethanol. This method is efficient and simple.     

One-Step Synthesis of Phosphorylated Vinylacethylene Derivatives

Russian Journal of General Chemistry - A one-step method for the preparation of 3-substituted 2-(diethylphosphoryl)but-1-en-3-ynes was developed based on the reaction of phosphorylated...     

Synthesis and Structure of Phosphorylated Nitronorbornenes

A procedure was suggested for preparing previously unknown phosphorylated nitronorbornenes from nitroethenephosphonates and cyclopentadienes. The structures of the products were studied by IR and ¹H and ^{3 1}P NMR spectroscopy. A single crystal X-ray diffraction study of bis(2-chloroethyl) 3-bromo-3-nitro- bicyclo[2.2.1]-5-heptene-2-phosphonate showed that the steric arrangement of the bicyclic fragment is typical of norbornenes. It is the endo-(NO₂) diastereomer in which Br and P(O)(OC₂H₄Cl)₂ substituents are eclipsed, and C²-C³ and C³-NO₂ bonds are noticeably elongated.     

Synthesis of Phosphorylated Nitrocyclohexenes and Nitronorbornenes

Russian Journal of General Chemistry -     

Chemoenzymatic Synthesis of a Phosphorylated Glycoprotein

The majority of lysosomal enzymes are targeted to the lysosome by post‐translational tagging with N‐glycans terminating in mannose‐6‐phosphate (M6P) residues. Some current enzyme replacement therapies (ERTs) for lysosomal storage disorders are limited in their efficacy by the extent to which the recombinant enzymes bear the M6P‐terminated glycans required for effective trafficking. Chemical synthesis was combined with endo‐β‐N‐acetylglucosaminidase (ENGase) catalysis to allow the convergent synthesis of glycosyl amino acids bearing M6P residues. This approach can be extended to the remodeling of proteins, as exemplified by RNase. The powerful synergy of chemical synthesis and ENGase‐mediated biocatalysis enabled the first synthesis of a glycoprotein bearing M6P‐terminated N‐glycans in which the glycans are attached to the peptide backbone by entirely natural linkages.     

Synthesis of Diterpene Indoles from Cyclopentenonepimaric Acid

Diterpene indoles were prepared by the Fischer reaction from cyclopentenonepimaric acid. The structures of the synthesized compounds were confirmed by IR and NMR spectroscopies.     

微波辅助一步合成2-取代吲哚

微波辐射下以取代苯胺1, 2-溴芳基乙酮2为原料, 在无催化剂条件下一步合成了一系列2-取代吲哚3. 该方法具操作简单、反应时间短、产率高等特点.     

A Versatile Synthesis of 3-Substituted Indoles

A variety of 3-substituted indoles are prepared from 1-methyl-3-(benzotriazol-1-ylalkyl)indoles (1), which are readily available either from the condensation of 3-methylindole with N-(benzotriazol-1-ylalkyl)carbamates or from the alkylation and silylation of lithiated 1-methyl-3-(benzotriazol-1-ylmethyl)indole (2).     

5-取代吲哚类化合物的合成

5－取代吲哚类化合物是一种重要的医药中间体。从古典的Fischer方法开始，有关合成5－取代吲哚类化合物的方法不断出现。本文对各种合成方法进行了介绍和评价。参考文献30篇。     

吲哚与含CF3氮杂对亚甲基苯醌的1,6-共轭加成反应合成含CF3的吲哚衍生物

以5 mol%布朗斯特酸(±)-BNPA为催化剂，含CF₃氮杂对亚甲基苯醌与吲哚为原料，通过1,6-共轭加成反应合成了7个结构新颖的含CF₃的吲哚类化合物，收率80%~87%，其结构经¹H NMR， ¹³C NMR， ¹⁹F NMR和HR-MS(ESI)表征，并对反应机理进行了探讨。     

Synthesis of Phosphorylated Derivatives of Enamino-Carbonyl Compounds

Abstract

The reactions of enaminocarbonyl compounds (1) with phosphorylisocyanates have been investigated. Experiment established that the reactions with the participation of amino group and (or) C-2 atom form respectively ureas (2) and (or) their vinylogs (3) depending on the structure (1) i.e. the reactions proceed in two competitive directions.     

A General and Scalable Synthesis of Polysubstituted Indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.     

A Synthesis of Phosphorylated 2,4-Dioxothiazolidine Derivatives

Abstract

The zwitterionic 1:1 intermediates generated from trialkyl phosphites and dialkyl acetylenedicarboxylates are trapped by 2,4-thiazolidinedione and 5-arylidene- 2,4-thiazolidinediones to produce dialkyl 2-(2,4-dioxothiazolidin-3-yl)-3-(dialkoxyphosphoryl) succinates and dialkyl 2-(5-arylidene-2,4-dioxothiazolidin-3-yl)-3-(dialkoxyphosphoryl) succinates in good yields.

GRAPHICAL ABSTRACT     

Synthesis and Properties of Phosphorylated 4-Methylpyrocatechol Derivatives

Procedures for preparing α-phosphorylated 4-methylpyrocatechols were developed. Diphenyl-(3,4-dimethoxybenzyl)phosphine oxide yields diphenyl(3,4-dihydroxybenzyl)phosphine oxide under the action of hydrobromic acid.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 3, 2005, pp. 415–416.Original Russian Text Copyright © 2005 by Ismagilov, Moskva, Shamsutdinova.     

Synthesis and Reaction Peculiarities of Phosphorylated Trifluoroethane Imines

Abstract

Convenient methods for C,N - mono- and biphosphorylated trifluoroethane imines have been developed. These are reactive synthons allowing important derivatives of aminophosphonic acids, fluorine- and phosphorus-containing heterocycles, vinylamides, etc. A rare example of a Perkov-type reaction involving trifluoromethyl group has been discovered.     

Selective Iron Catalyzed Synthesis of N-Alkylated Indolines and Indoles

Whereas iron catalysts usually promote catalyzed C3-alkylation of indole derivatives via a borrowing-hydrogen methodology using alcohols as the electrophilic partners, this contribution shows how to switch the selectivity towards N-alkylation. Thus, starting from indoline derivatives, N-alkylation was efficiently performed using a tricarbonyl(cyclopentadienone) iron complex as the catalyst in trifluoroethanol in the presence of alcohols leading to the corresponding N-alkylated indoline derivatives in 31–99 % yields (28 examples). The one-pot, two-step strategy for the selective N-alkylation of indolines is completed by an oxidation to give the corresponding N-alkylated indoles in 31–90 % yields (15 examples). This unprecedented oxidation methodology involves an iron salt catalyst associated with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and a stoichiometric amount of t-BuOOH at room temperature.