89844-77-9

Upstream product

• 38436-36-1 2-nitro-3-phenylprop-2-enenitrile 
• 622-37-7 Phenyl azide 
• 1823-99-0 3-amino-3-phenylacrylonitrile 
• 614-16-4 Benzoylacetonitrile 
• 98-80-6 phenylboronic acid 
• 4360-47-8 cinnamonitrile 
• 62-53-3 aniline 

Downstream Products

• 51072-85-6 2-phenyl-1H-indole-3-carbonitrile 
• 4900-34-9 1,5-diphenyl-1H-1,2,3-triazole-4-carboxylic acid 

Relevant academic research and scientific papers

Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) is an active catalyst in C?H-amination but also in proton-transfer catalysis. Herein, we describe the successful use of this complex as a proton-transfer catalyst in the cyclocondensation reaction between azides and ketones to the corresponding 1,2,3-triazoles. Cross-experiments indicate that the proton-transfer catalysis is significantly faster than the nitrene-transfer catalysis, which would lead to the C?H amination product. An example of a successful sequential Dimroth triazole–indoline synthesis to the corresponding triazole-substituted indolines is presented.

Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.

Lewis base catalyzed aerobic oxidative intermolecular azide-zwitterion cycloaddition

The discovery of a novel aerobic oxidative intermolecular azide-zwitterion reaction catalyzed by an organocatalyst is presented. It is demonstrated that the merger of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene and electrondeficient olefins generates reactive zwitterion intermediates, which readily participate in cycloaddition reactions with an array of azides, thus providing facile entry to fully or highly substituted 1,2,3-triazole frameworks. The reaction features an excellent substrate scope, and the products are obtained with high yields and excellent regioselectivities. It is demonstrated that some of these products can be transformed into pharmaceutically important agents. In addition to the experimental results, a detailed mechanistic survey is also provided, including MS studies rationalizing the origin of regioselective control.

Novel synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via a one-pot three-component reaction of boronic acids, azide, and active methylene ketones

A series of 1-aryl-5-trifluoromethyl (or difluoromethyl)-1,4,5- trisubstituted 1,2,3-triazoles were synthesized in high yield by a novel one-pot three-component reaction of arylboronic acids, sodium azide, and active methylene ketones, such as ethyl 4,4-difluoroacetoacetate or ethyl 4,4,4-trifluoroacetoacetate in the presence of Cu(OAc)2 and piperidine using a DMSO/H2O (10/1) mixture as solvent.

Amine-catalyzed [3+2] Huisgen cycloaddition strategy for the efficient assembly of highly substituted 1,2,3-triazoles

An enamine-catalyzed strategy has been utilized to fully promote the Huisgen [3+2] cycloaddition with a broad spectrum of carbonyl compounds and azides, thereby permitting the efficient assembly of a vast pool of highly substituted 1,2,3-triazoles. In par

Organocatalytic enamide-azide cycloaddition reactions: Regiospecific synthesis of 1,4,5-trisubstituted-1,2,3-triazoles

Heterocycles in one click: A novel organocatalytic enamide-azide cycloaddition reaction has been developed. This synthetic procedure represents a new method for the efficient construction of 1,4,5-trisubstituted-1,2,3- triazoles under mild reaction condit

Reactions of 2-Benzylidenemalononitrile and 2-Nitro-3-phenylacrylonitrile with Aryl Azides

Reactions of 2-benzylidenemalononitrile and 2-nitro-3-phenylacrylonitrile with aryl azides in diethyl ether at room temperature gave mixtures of regioisomeric 1(3)-aryl-5-phenyl-4,5-dihydro-1(3)H-1,2,3- triazole-4,4- dicarbonitriles and 1-aryl-5(4)-phenyl-1H-1,2,3-triazole-5(4)-carbonitriles, respectively. 2-Benzylidenemalononitrile reacted with the same arylazides on heating in boiling chloroform to produce 1-aryl-2- phenylaziridine-2,2- dicarbonitriles. Pleiades Publishing, Ltd., 2011.

REACTIONS DES METHYLAZIDE ET PHENYLAZIDE AVEC QUELQUES ALCYNES ET OLEFINES α-NITREES. SYNTHESE REGIOSPECIFIQUE DES 1,2,3 TRIAZOLES

The reactions of alkynes and α-nitro-olefines with methylazide and phenylazide was studied.In contrast to known reactions with alkynes which are non-regioselective, methylazide and phenylazide react regiospecifically with α-nitro-olefines and give only one type of triazole after elimination of HNO2.These reactions are very useful synthetic approaches to 1,2,3 triazoles.