36193-65-4 | - Indole Building Blocks

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The pyrolysis of aliphatic alpha-amino acids, glutamine, glutamic and aspartic acids, and formation of heterocyclic and polycyclic aromatic hydrocarbons (N-PACs and PAHs) were studied. Each amino acid was first pyrolyzed at 300 C to obtain a low-temperature tar (LTT) and a low-temperature char (LTC). The LTC was then pyrolyzed at 625 C to obtain the corresponding high-temperature tar (HTT) and high-temperature char (HTC). The tars were separately subjected, in some cases, to temperatures in the range 700-870 C to study secondary reactions. Oligomers of aspartic acid and glutamic acid were also pyrolyzed. The tars were analyzed by gas chromatography/mass spectrometry. Glutamic acid and glutamine underwent significant decomposition to volatile products at 300 C but aspartic acid required higher temperature. The heterocyclic compounds were primarily single-ring compounds comprised of five- or six-member heterocycles in the absence of secondary reactions, and up to four rings after the secondary pyrolysis. The PACs included nitriles from glutamine and glutamic acid and PAHs from aspartic acid. For aspartic acid, the results from oligomers were similar to those from the monomer, whereas the results from the glutamic acid oligomer were slightly different from glutamic acid. All three acids appeared to break down to smaller “building blocks” and then pyrosynthesize the N-PACs and PAHs.

Reference：
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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The reactions of 2-(tosylamino)benzyltrimethylammonium halides (1) with dimethylsulfonium 2-oxo-2-phenylethylide (6b), dimethylsulfonium 2-ethoxy-2-oxo-ethylide (6c) and dimethylsulfonium cyanomethylide (6d) are useful synthetic routes to 2-substituted indoles (8b-d). The relationship between reaction conditions and selectivity is discussed.

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Methods of obtaining ketones and enamino esters have been developed on the basis of reactions of 1-(1-phenylethyl)indole-2-carbonitrile with organomagnesium and organozinc compounds. Removal of a benzyl group from the indole nitrogen atom by the Grignard reagent has been discovered.

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Manganese(III)-mediated oxidative radical addition of malonates to 2-cyanoindoles

2-Cyanoindole and N-methyl-2-cyanoindole undergo manganese(III)-mediated radical addition with activated methylene and methine compounds. Products of the methylene addition underwent additional oxidation during the course of the reaction to furnish the corresponding acetoxy compounds. Several structures were confirmed by X-ray crystallography.

Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Application of 36193-65-4, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.36193-65-4, Name is 1H-Indole-2-carbonitrile, molecular formula is C9H6N2. In a Article£¬once mentioned of 36193-65-4

A concise approach to substituted Quinazolin-4(3H)-one natural products catalyzed by Iron(III) Chloride

A novel and efficient method for the synthesis of various Quinazolin-4(3H)-one natural products was developed utilizing Iron(III) Chloride catalyzed reaction as a key step. Circumdatin H, Bouchardatine, 8-Norrutaecarpine and, Luotonin B and E are few natural products synthesized by this methodology.

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A concise approach to substituted Quinazolin-4(3H)-one natural products catalyzed by Iron(III) Chloride

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Transition metal-catalyzed site- and regio-divergent C-H bond functionalization

Recent advances in transition metal-catalyzed C-H bond functionalization have profoundly impacted synthetic strategy. Since organic substrates typically contain several chemically distinct C-H bonds, controlling the regioselectivity of C-H bond functionalization is imperative to harness its full potential. Moreover, the ability to alter reaction pathways to selectively functionalize different C-H bonds in a substrate represents a greater opportunity and challenge. The choice of catalysts, ligands, solvents, and even more subtle variations of the reaction conditions have been shown to allow the formation of regioisomeric C-H functionalization products starting from the same precursors. This review describes recent advances in transition metal-catalyzed divergent C-H bond functionalization that highlight its potential in organic synthesis.

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36193-65-4, 1H-Indole-2-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A Preparation of (26) where R10 is 2-Cyanoindole A mixture of 3.0 g (0.02 mol) of 2-cyanoindole, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110 C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluding with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-2-cyanoindole as an oil.

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Reference£º
Patent; Syntex (U.S.A.) Inc.; US5380739; (1995); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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General procedure: Cyanoindole 6 (40 mg, 0.256 mmol, 1 equiv.), Mn(OAc)3.2H2O (345 mg, 1.29 mmol, 5 equiv),and diethyl malonate (205 mg, 1.28 mmol, 5 equiv) were dissolved in aceticacid (10 mL) and heated to reflux for 2 h. After TLC indicated complete consumption of the starting indole, the reaction was poured into water (200 mL) and extracted with ethyl acetate (3 50 mL). The combined organic extracts were washed with water (3 100 mL), brine (1 100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. The product was purified via flash chromatography (silica gel, hexanes:EtOAc 4:1)to afford 15 as a white solid (90%);20

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Reference£º
Article; Lopchuk, Justin M.; Montgomery, William L.; Jasinski, Jerry P.; Gorjifard, Sayeh; Gribble, Gordon W.; Tetrahedron Letters; vol. 54; 45; (2013); p. 6142 – 6145;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles