436-53-3

Upstream product

• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 100-63-0 phenylhydrazine 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 98-80-6 phenylboronic acid 
• 86839-11-4 2-(p-Fluorbenzoylamino)benzophenon 
• 462-06-6 fluorobenzene 
• 103-80-0 phenylacetyl chloride 
• 405-29-8 (4-fluorophenyl)phenylacetylene 
• 62-53-3 aniline 
• 98-95-3 nitrobenzene 
• 591-50-4 iodobenzene 
• 536-74-3 phenylacetylene 
• 98-09-9 benzenesulfonyl chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 

Relevant academic research and scientific papers

An Oxidant- And Catalyst-Free Synthesis of Dibenzo[ a, c ]carbazoles via UV Light Irradiation of 2,3-Diphenyl-1 H -indoles

An efficient methodology for the synthesis of dibenzo[a,c]- carbazoles via annulation of 2,3-diphenyl-1H-indoles in EtOH under UV light irradiation (λO = 365 nm) along with hydrogen evolution is described. This method exhibits the advantages of mild reaction conditions, no requirement of any oxidants and catalysts, and release of hydrogen as the only byproduct. Notably, the mechanism investigation confirms that the trans-4b,8a-dihydro-9H-dibenzo[a,c]carbazole intermediate could convert into cis-4b,8a-dihydro-9H-dibenzo[a,c]carbazole, which relies on the nitrogen atom of the indole ring. This is followed by intramolecular dehydrogenation which yields the dibenzo[a,c]carbazoles. 2021. Thieme. All rights reserved.

Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides

A simple and practical method for the synthesis of phosphoryl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and benzimidazo[2,1-a]isoquinolin-6(5H)-ones through manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles or 2-arylbenzimidazoles with disubstituted phosphine oxides was developed. In this transformation, new C-P bond and C-C bond were constructed simultaneously under silver-free conditions, exhibiting a broad substrate scope. It was noted that not only diarylphosphine oxides but also dialkyl and arylalkyl-phosphine oxides were compatible with the conditions. This journal is

Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with o-azidoarylalkynes: a regiospecific route to unsymmetrical 2,3-disubstituted indoles

A visible-light-catalyzed synthesis of unsymmetrical 2,3-diaryl-substituted indoles from arylsulfonyl chlorides and o-azidoarylalkynes at room temperature has been discovered. This transformation exhibits excellent substrate scope and functional group tolerance. The use of inexpensive eosin Y as the catalyst with easy operation makes this protocol very practical.

Transition-metal-free, visible-light-mediated cyclization of: O -azidoarylalkynes with aryl diazonium salts

Visible light along with 3 mol% eosin Y catalyzes the cyclization reaction of o-azidoarylalkynes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and o-azidoarylalkynes. The general and easy procedure provides a transition-metal-free alternative for the formation of unsymmetrical 2,3-diaryl-substitued indoles.

Rhodium-Catalyzed C-H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substituted Indoles

The direct C-H annulation of anilines or related compounds with internal alkynes provides straightforward access to 2,3-disubstituted indole products. However, this transformation proceeds with poor regioselectivity in the synthesis of unsymmetrically 2,3-diaryl substituted indoles. Herein, we report the rhodium(III)-catalyzed C-H annulation of nitrones with symmetrical diaryl alkynes as an alternative method to prepare 2,3-diaryl-substituted N-unprotected indoles with two different aryl groups. One of the aryl substituents is derived from N?C-aryl ring of the nitrone and the other from the alkyne substrate, thus providing the indole products with exclusive regioselectivity.

Phosphine-free thiopseudourea-Pd(II) complex catalyzed Larock heteroannulation of 2-haloamines with internal alkynes

We examined the Pd-catalyzed heteroannulation of 2-haloamines with internal alkynes under phosphinefree conditions. The thiopseudourea palladium(II) complex (5) found to be an efficient catalyst for the Pd induced heteroannulation. Achieved high turnover number for the heteroannulation reactions of internal alkynes with 2-iodoaniline. A variety of 2-bromoanilines and N-tosyl substituted 2-bromoanilines effectively reacted with different substituted internal alkynes to give the corresponding indoles in good to high yields (1:1 ratio of regioisomers).

Palladium-catalyzed reaction of arylamine and diarylacetylene: Solvent-controlled construction of 2,3-diarylindoles and pentaarylpyrroles

By choosing DMF and dioxane as solvent, skeletons of indoles and pyrroles were constructed from alkynes and amines in the presence of PdCl2, respectively. These Pd-catalyzed reactions were phosphane-free with high atom efficiency and could be conducted under mild basic conditions. The proposed mechanism for the selective formation of indoles and pyrroles in different solvents is also discussed in this paper. Two different kinds of Pd-catalyzed cyclizations, leading to the construction of 2,3-diarylindole and pentaarylpyrrole from the same alkyne and aniline starting materials, were approached by choosing different solvents. The mechanisms for these solvent-controlled reactions are proposed and discussed. Copyright

Practical method for synthesis of 2,3-disubstituted indole derivatives promoted by β-(benzotriazol-1-yl)allylic O-stannyl ketyl radicals

Treatment of β-aryl-β-(benzotriazol-1-yl)-α-primary alkyl (or aryl)-α,β-unsaturated ketones 1 with n-Bu3SnH (4 equiv) in a catalytic amount of AIBN in PhH at reflux afforded 3-alkyl (or aryl)-2-arylindoles 8 in good yields. However, when tert-butyl group is bonded at α-position, 3-acyl (or aroyl)-2-arylindoles 9 were obtained as major products along with phenanthridines 5 as minor products.

A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine

(Chemical Equation Presented) The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or α,β-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4- dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.

Facile preparation of 2,3-disubstituted indole derivatives through low-valent titanium induced intramolecular reductive coupling reactions of acylamido-carbonyl compounds

An efficient synthesis of 2,3-disubstituted indole derivatives through low-valent titanium induced reductive cyclisation of suitably substituted acylamido-carbonyl compounds is described.